Azo dyes with sulfate groups on the diazotized 2-amino thiazol and 5-amino isothiazol moiety and with aniline, tetrahydroquinoline and benzomorpholine couplers

ABSTRACT

This invention relates to azo dyes particularly useful for dyeing polyamide fiber, wool and the like, in which the diazotized amino component bears sulfated hydroxyalkoxycarbonyl or N-(hydroxyalkyl)carbamoyl groups on its ring. These dyes have excellent dyeing properties on polyamide fibers and also impart color to cellulose acetate fibers and wool. The dyes correspond to the formula:   &lt;IMAGE&gt;  +TR  &lt;IMAGE&gt;  wherein R1 and R represent a large variety of groups; X&#39; is O, NH, N(alkyl)- or N(aryl)-; Z is selected from straight- or branched-chain alkylene which may be substituted, for example, with phenyl, halogen, OSO3M, alkoxy, aryloxy and the like; M is H, Na, K or NH4; n is 1 or 2; and the coupler C is selected from a variety of couplers including anilines, tetrahydroquinolines, phenols and the like.

This invention concerns novel dyes in which the diazo moieties contain sulfate groups. These dyes are substantially water soluble and are particularly useful for dyeing polyamide, wool and the like, and exhibit excellent properties, including fastness to light and dyeability.

The dyes of this invention correspond to the general formulae: ##STR2## wherein n is 1, R¹ and R are defined below; C is the coupler portion of the molecule; X' is O, NH, N(alkyl)-, or N(aryl)-; Z is selected from straight- or branched-chain alkylene, which may be substituted, for example, with phenyl, halogen, OSO₃ M, alkoxy or aryloxy groups, --CH₂ (CH₂)_(m) V--CH₂ (CH₂)_(p) --, where m is 1, 2 or 3, p is 0, 1, 2 or 3, and V is O, S, SO₂, --SO₂ NH--, --SO₂ N(alkyl)--, --SO₂ N(aryl), --N(SO₂ aryl)--, --NH, --NHCO--, --NHCONH, --N(SO₂ alkyl), or --CON(alkyl); M is H, Na, K or NH₄ ; and n is 1 or 2.

More particularly, the dyes are of the above formulae wherein the thiazol-2-yl ring may have the substituent R¹ selected from hydrogen, alkyl, cyclohexyl, 2-thienyl, 2-furyl, phenyl, and phenyl substituted with alkoxy, thiocyano, alkylthio, carbamoyl, alkylcarbamoyl, acyl, alkylsulfonyl, sulfamoyl, SO₂ NH(alkyl), SO₂ N(dialkyl), alkylsulfonamido, acylamido, halogen, trifluoromethyl or SO₃ (aryl); the isothiazol-5-yl ring may have the substituent R selected from hydrogen, halogen, alkyl, alkylsulfonyl, phenyl, and phenyl substituted with alkyl, alkoxy or halogen; and the coupler C is selected from ##STR3## wherein R² and R¹⁴ each represents up to three groups selected from hydrogen, fluorine, chlorine, bromine, alkyl, cycloalkyl, alkoxy, phenoxy, alkylthio, arylthio, and radicals having the formula --NH--X--R³ in which X is --CO--, --COO--, or --SO₂ -- and R³ is selected from alkyl and alkyl substituted with halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyloxy, and alkoxy, and when X is --CO--, R³ also is selected from hydrogen, amino, alkylamino, alkylcarbamoyl, dialkylamino, arylamino, aryl, and furyl;

R⁴ and R⁵ are each selected from hydrogen, alkyl, aryl, cycloalkyl, and R⁴ and R⁵ together represent a single, combined group --CH₂ CH₂ CH₂ CH₂ CH₂ --, --CH₂ CH₂ OCH₂ CH₂ --, --CH₂ CH₂ --S--CH₂ CH₂ --, and --CH₂ CH₂ --SO₂ --CH₂ CH₂ --;

R⁸ is one or two groups each selected from hydrogen, alkyl and alkyl substituted with --CN, alkoxy, alkoxycarbonyl, alkoxycarbonyloxy, phenyl, cyclohexoxy --OH, --Cl and Br;

R⁹, R¹⁰ and R¹¹ are each selected from hydrogen, alkyl, phenyl, or phenyl substituted with 1-3 groups selected from Cl, Br, alkyl or alkoxy, alkylthio, benzylthio, cyclohexylthio, phenylthio and substituted phenylthio;

Q and Q' are each selected from --CO--, --SO₂ --, or --CN; R¹² and R¹³ are each selected from hydrogen, alkyl, hydroxyalkyl, alkoxy, alkoxycarbonylamino, trifluoromethyl, phenyl or phenyl substituted with 1-3 groups selected from Cl, Br, alkyl or alkoxy, alkoxycarbonylalkyl, cyanolalkyl, amino, haloalkyl, alkylamino, alkylthio, benzylthio, cyclohexylthio, phenylthio and substituted phenylthio; R¹² and R¹³ may combine to form an alkylene bridge of 2 or 3 carbons, or to form an arylene or cycloalkylene radical of 5-6 carbons connecting Q and Q'; R¹⁶ and R¹⁷ are selected from hydrogen, cycloalkyl, aryl, alkyl, and alkyl substituted with alkoxy, hydroxy, alkoxyalkoxy, hydroxyalkoxy, carbamoyl, sulfamoyl, acylamido, or alkenylsulfonyl, and aryl substituted with hydroxyalkyl; e is 1 or 2; and t and t' are each 1 or zero. It is noted that when t or t' is zero, the corresponding Q or Q' group is --CN;

Each of the aliphatic portions of the above alkyl, cycloaliphatic, alkoxy, alkanoyl and the like groups, as well as the aryl and aryloxy groups, may be substituted further with up to three of the following: hydroxy; halogen; cyano; succinimido; glutarimido; phthalimido; 2-pyrrolidono; cyclohexyl; phenyl or phenyl substituted with alkyl, alkoxy, halogen, alkanoylamino; cyano or alkoxycarbonyl; alkanoylamino; sulfamoyl; alkylsulfamoyl; vinylsulfonyl; acrylamido; phthalimidinyl; benzoylsulfonicimidyl; alkylsulfonamido; phenylsulfonamido; alkoxycarbonylamino; alkylcarbamoyloxy; alkoxycarbonyl; alkoxycarbonyloxy; ##STR4## wherein Y is --NH--, --NH--alkyl-, --O--, --S--, or --CH₂ O--; --S--R⁶ wherein R⁶ is alkyl, phenyl, phenyl substituted with halogen, alkyl, alkoxy, alkanoylamino, cyano, or alkoxycarbonyl, pyridyl, pyrimidinyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, triazolyl, or ##STR5## --SO₂ R³ ; --COOR³ ; --OXR³ ; --NH--X--R³ ; --X--R³ ; --OCO--R³ ; --CONR⁷ R⁷ ; --SO₂ NR⁷ R⁷ ; wherein R³ and X are as defined above and each R⁷ is selected from H and R³ ; alkoxy; alkoxy substituted with hydroxy, cyano, alkanoyloxy, or alkoxy; phenoxy or phenoxy substituted with one or more of alkyl, alkoxy or halogen. All of the aliphatic portions of the various groups herein contain from 1-6 carbons, and are straight or branched chain.

The dyes of this invention impart red to blue shades on fibers, particularly polyamides, and are especially useful for dyeing polyamide (nylon) carpets, giving good fastness to light, ozone, oxides of nitrogen, washing, sublimation, crocking and the like, and having good leveling, transfer, exhaustion, and build properties.

The couplers used in this invention are prepared according to known procedures. The dyes may be prepared by reacting the coupler in conventional manner with a diazonium salt which contains one or two carbalkoxy groups. The product is reacted first with an aminoalcohol H--X'--Z--OH (X' is NH, Z is alkylene) to convert to a N--(hydroxyalkyl)carbamyl group, or with an alkanediol H--X'--Z--OH (X' is O, Z is alkylene) to convert to a hydroxyalkoxycarbonyl group. Subsequently, the material is reacted with concentrated sulfuric acid to form the sulfate ester: ##STR6##

Alternatively, a diazotizable amine containing a hydroxyalkoxycarbonyl group or a N-(hydroxyalkyl)carbamyl group may be sulfated before diazotization and coupling:

This invention will be further illustrated by the following examples although it will be understood that these examples are included merely for purposes of illustration and are not intended to limit the scope of the invention. The compounds listed in the tables below can be prepared by procedures well known to the art.

                                      TABLE 1                                      __________________________________________________________________________      ##STR8##                                                                      R.sup.1      R.sup.2     R.sup.4   R.sup.5    X'Z          M                   __________________________________________________________________________     H            2-CH.sub.3, 5-NHCOCH.sub.3                                                                 H         C.sub.2 H.sub.5                                                                           NHC.sub.2 H.sub.4                                                                           Na                  H            H           C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 N(COCH.sub.3).sub.2                                                       N(CH.sub.3)C.sub.2 H.sub.4                                                                  "                   H            3-CH.sub.3  C.sub.2 H.sub.4 Cl                                                                       C.sub.2 H.sub.4 CN                                                                        NHC.sub.2 H.sub.4                                                                           K                   H            "           "         "          NHCH.sub.2CH(C.sub.6                                                           H.sub.5)     K                   C.sub.6 H.sub.5                                                                             3-CH.sub.3  C.sub.2 H.sub.4 OH                                                                       C.sub.2 H.sub.4 OH                                                                        OC.sub.2 H.sub.4                                                                            Na                  "            3-NHCOCH.sub.3                                                                             C.sub.2 H.sub.5                                                                          C.sub.2 H.sub. 4 CN                                                                       NHC.sub.2 H.sub.4 OC.sub.2                                                     H.sub.4      Na                  "            2-OCH.sub.3, 5-NHCOCH.sub.3                                                                C.sub.2 H.sub.4 OCOCH.sub.3                                                              C.sub.2 H.sub.4 OCOCH.sub.3                                                               NHC.sub.2 H.sub.4                                                                           NH.sub.4            H            3-Cl        C.sub.2 H.sub.4 OH                                                                       C.sub.6 H.sub.13                                                                          OC.sub.2 H.sub.4                                                                            K                   CH.sub.3     2-Cl        H         C.sub.2 H.sub.4 OH                                                                        OC.sub.2 H.sub.4                                                                            K                   "            2-CH.sub.3, 3-Cl                                                                           H         CH.sub.2 C.sub.6 H.sub.5                                                                  NHC.sub.3 H.sub.6                                                                           K                   "            H           C.sub.2 H.sub.4 OH                                                                       C.sub.2 H.sub.4 CN                                                                        OC.sub.2 H.sub.4                                                                            NH.sub.4            "            H           C.sub.2 H.sub.4 OSO.sub.3 K                                                              C.sub.2 H.sub.5                                                                           NHC.sub.2 H.sub.4                                                                           K                   CH.sub.2 Cl  3-CH.sub.3  C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 NHCOCH.sub.3                                                              "            "                    ##STR9##    3-NHCOCH.sub.3                                                                             "         C.sub.2 H.sub.4 CONH.sub.2                                                                "            "                    ##STR10##   H           "         C.sub.2 H.sub.4 NHCOCH.sub.3                                                              N(C.sub.6 H.sub.5)C.sub.2                                                      H.sub.4      Na                  H            "           "         H          NHC.sub.2 H.sub.4                H            H           CH.sub.2 CH.sub.2OCH.sub.2 CH.sub.2                                                                 NHC.sub.2 H.sub.4                                                                           Na                  H            H           CH.sub.2 CH.sub.2SCH.sub.2 CH.sub.2                                                                 NHC.sub.2 H.sub.4                                                                           Na                  H            H           CH.sub.2 CH.sub.2SO.sub.2CH.sub.2 CH.sub.2                                                          NHC.sub.2 H.sub.4                                                                           Na                  H            H           CH.sub.2 CH.sub.2NHCH.sub.2 CH.sub.2                                                                NHC.sub.2 H.sub.4                                                                           Na                  C.sub.6 H.sub.4p-C.sub.6 H.sub.11                                                           H           CH.sub.2 CH.sub.2N(COCH.sub.3)CH.sub.2 CH.sub.2                                                     NHC.sub.2 H.sub.4                                                                           Na                  C.sub.6 H.sub.4p-C.sub.2 H.sub.5                                                            3-CH.sub.3  H         C.sub.2 H.sub.4 SO.sub.2 NH.sub.2                                                         NHC.sub.2 H.sub.4                                                                           Na                  C.sub.6 H.sub.4p-OCH.sub.3                                                                  2-OC.sub.6 H.sub.5                                                                         C.sub.2 H.sub.4 CN                                                                       C.sub.2 H.sub.4 N(COCH.sub.3).sub.2                                                       "            "                   C.sub.6 H.sub.4p-SCN                                                                        2-SCH.sub.3 C.sub.2 H.sub.4 OCOCH.sub.3                                                              C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2                                             H.sub.5    NHC.sub.2 H.sub.5                                                                           K                   C.sub.6 H.sub.4p-SC.sub.2 H.sub.5                                                           3-SC.sub.6 H.sub.5                                                                         CONH.sub.2                                                                               C.sub.2 H.sub.4 SO.sub.2 NH(C.sub.2                                            H.sub.5)   NHCH.sub.2CH(C.sub.6                                                           H.sub.5)     K                   C.sub.6 H.sub.4p-CONH.sub.2                                                                 3-NHCOOCH.sub.3                                                                            C.sub.2 H.sub.4 OH                                                                       C.sub.2 H.sub.4 OH                                                                        OC.sub.2 H.sub.4                                                                            Na                  C.sub.6 H.sub.4p-CH.sub.3                                                                   3-NHSO.sub.2 CH.sub.3                                                                      C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 CN                                                                        NHC.sub.2 H.sub.4 OC.sub.2                                                     H.sub.4      Na                  C.sub.6 H.sub.4o-CONHCH.sub.3                                                               2-OCH.sub.3, 5-NHCOCH.sub.3                                                                C.sub.2 H.sub.4 OCOCH.sub.3                                                              C.sub.2 H.sub.4 OCOCH.sub.3                                                               NHC.sub.2 H.sub.4                                                                           NH.sub.4            C.sub.6 H.sub. 4o-C.sub.6 H.sub.11                                             C.sub.6 H.sub.4o-CH.sub.3                                                                   3-NHCOCH.sub.2 Cl                                                                          C.sub.2 H.sub.4 OH                                                                       C.sub.6 H.sub.13                                                                          OC.sub.2 H.sub.4                                                                            K                   C.sub.6 H.sub.4o-SO.sub.2 CH.sub.3                                                          3-NHCOC.sub.2 H.sub.4 OH                                                                   H         C.sub.2 H.sub.4 OH                                                                        OC.sub.2 H.sub.4                                                                            K                   C.sub.6 H.sub.4o-Cl                                                                         2-CH.sub.3, 3-Cl                                                                           H         CH.sub.2 C.sub.6 H.sub.5                                                                  NHC.sub. 3 H.sub.6                                                                          K                   C.sub.6 H.sub.4o-SO.sub.2 NHCH.sub.3                                                        2-NHCONHC.sub.2 H.sub.5                                                                    C.sub.2 H.sub.4 OH                                                                       C.sub.2 H.sub.4 CN                                                                        OC.sub.2 H.sub.4                                                                            NH.sub.4            C.sub.6 H.sub.4m-NHSO.sub.2 CH.sub.3                                                        2-NHCON(C.sub.2 H.sub.5).sub.2                                                             C.sub.2 H.sub.4 OSO.sub.3 K                                                              C.sub.2 H.sub.5                                                                           NHC.sub.2 H.sub.4                                                                           K                   C.sub.6 H.sub.4m-NHCOCH.sub.3                                                               3-CH.sub.3  C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 NHCOCH.sub.3                                                              "            "                   C.sub.6 H.sub.4m-CF.sub.3                                                                   3-NHCOCH.sub.3                                                                             "         C.sub.2 H.sub.4 CONH.sub.2                                                                "            "                   C.sub.6 H.sub.4m-SO.sub.3 C.sub.6 H.sub.5                                                   H           "         C.sub.2 H.sub.4 NHCOCH.sub.3                                                              "            Na                  __________________________________________________________________________

                                      TABLE 2                                      __________________________________________________________________________      ##STR11##                                                                     R.sup.1  R.sup.2   R.sup.8 R.sup.4  X'Z         M                              __________________________________________________________________________     H        7-CH.sub.3                                                                               2-CH.sub.3                                                                             C.sub.2 H.sub.4 OH                                                                      OC.sub.2 H.sub.4                                                                           Na                             H        7-CH.sub.3                                                                               2-CH.sub.3                                                                             C.sub.2 H.sub.4 OSO.sub.3 K                                                             NHC.sub.2 H.sub.4                                                                          K                              H        H         H       C.sub.2 H.sub.4 OC.sub.6 H.sub.11                                                       OC.sub.2 H.sub.4                                                                           Na                             H        5-CH.sub.3                                                                               H       C.sub.4 H.sub.9                                                                         NHC.sub.2 H.sub.4                                                                          Na                             C.sub.6 H.sub.5                                                                         7-CH.sub.3                                                                               2-CH.sub.3                                                                             C.sub.2 H.sub.4 NHCOCH.sub.3                                                            "           "                              "        7-CH.sub.3                                                                               2,2,4-(CH.sub.3).sub.3                                                                 "        N(C.sub.2 H.sub.5)C.sub.2                                                                  ".sub.4                        "        8-CH.sub.3                                                                               H       C.sub.2 H.sub.4 Cl                                                                      OC.sub.2 H.sub.4                                                                           NH.sub.4                       H        H         2,2,4-(CH.sub.3).sub.3                                                                 C.sub.2 H.sub.4 OCH.sub.3                                                               OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                          K                              CH.sub.3 7-NHCOCH.sub.3                                                                           "       C.sub.2 H.sub.4 Br                                                                      NHC.sub.2 H.sub.4                                                                          K                              "        "         5-CH.sub.3                                                                             CH.sub.2 CH(OH)CH.sub.2 OH                                                              OC.sub.2 H.sub.4                                                                           K                              "        7-CH.sub.3                                                                               2-CH.sub.3                                                                             CH.sub.3 NHC.sub.2 H.sub.4                                                                          K                              "        7-C.sub.6 H.sub.11                                                                       3-OH    C.sub.2 H.sub.4 SO.sub.2 NH.sub.2                                                       NHC.sub.2 H.sub.4                                                                          Na                             CH.sub.2 Cl                                                                             7-OC.sub.6 H.sub.5                                                                       3-CN    C.sub.2 H.sub.4 N(COCH.sub.3).sub.2                                                     N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          "                               ##STR12##                                                                              7-SCH.sub.3                                                                              3-OCOCH.sub.3                                                                          C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5                                              NHC.sub.2 H.sub.4                                                                          K                               ##STR13##                                                                              7-SC.sub.6 H.sub.5                                                                       2-CH.sub.3                                                                             C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5                                              NHCH.sub. 2CH(C.sub.6 H.sub.5)                                                             K                              H        7-NHCOOCH.sub.3                                                                          "       C.sub.2 H.sub.4 OH                                                                      OC.sub.2 H.sub.4                                                                           Na                             H        7-NHSO.sub.2 CH.sub.3                                                                    2-C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.4 CN                                                                      NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         Na                             H        7-OCH.sub.3                                                                              3-OCOCH.sub.3                                                                          C.sub.2 H.sub.4 OCOCH.sub.3                                                             NHC.sub.2 H.sub.4                                                                          NH.sub.4                       H        7-NHCOCH.sub.2 Cl                                                                        3-OH    C.sub.6 H.sub.13                                                                        OC.sub.2 H.sub.4                                                                           K                              H        7-NHCOC.sub.2 H.sub.4 OH                                                                 3-CONH.sub.2                                                                           C.sub.2 H.sub.4 OH                                                                      OC.sub.2 H.sub.4                                                                           K                              C.sub.6 H.sub.4p-C.sub.6 H.sub.11                                                       7-CH.sub.3, 5-Cl                                                                         3-Cl    CH.sub.2 C.sub.6 H.sub.5                                                                NHC.sub.3 H.sub.6                                                                          K                              C.sub.6 H.sub.4p-C.sub.2 H.sub.5                                                        7-NHCONHC.sub.2 H.sub.5                                                                  3-OC.sub.6 H.sub.5                                                                     C.sub.2 H.sub.4 CN                                                                      OC.sub.2 H.sub.4                                                                           NH.sub.4                       C.sub.6 H.sub.4p-OCH.sub.3                                                              7-NHCON(C.sub.2 H.sub.5).sub.2                                                           3-OC.sub.6 H.sub.5                                                                     C.sub.2 H.sub.5                                                                         NHC.sub.2 H.sub.4                                                                          K                              C.sub.6 H.sub.4p-SCN                                                                    7-CH.sub.3                                                                               3-SC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.4 NHCOCH.sub.3                                                            "           "                              C.sub.6 H.sub.4p-SC.sub.2 H.sub.5                                                       7-NHCOCH.sub.3                                                                           3-CONHC.sub.2 H.sub.5                                                                  C.sub.2 H.sub.4 CONH.sub.2                                                              "           "                              C.sub.6 H.sub.4p-CONH.sub.2                                                             H         3-OCH.sub.3                                                                            C.sub.2 H.sub.4 NHCOCH.sub.3                                                            "           Na                             __________________________________________________________________________

                                      TABLE 3                                      __________________________________________________________________________      ##STR14##                                                                     R.sup.1    R.sup.2     R.sup.8   R.sup.4     X'Z          M                    __________________________________________________________________________     H          6-NHCOCH.sub.3                                                                             3-CH.sub.3                                                                               C.sub.2 H.sub.5                                                                            NHC.sub.2 H.sub.4                                                                           Na                   H          6-CH.sub.3  3-CH.sub.3                                                                               C.sub.2 H.sub.5                                                                            OC.sub.2 H.sub.4                                                                            Na                   H          6-Cl          "       C.sub.2 H.sub.4 OH                                                                         OC.sub.2 H.sub.4                                                                            K                    H          6-Br        2,3-di-CH.sub.3                                                                          C.sub.2 H.sub.4 SO.sub.2 NH.sub.2                                                            "          NH.sub.4             C.sub.6 H.sub.5                                                                           6-F         3-CH.sub.3                                                                                 "         NHC.sub.2 H.sub.4                                                                           K                    "          H           2-CH.sub.2 OH                                                                            CH(CH.sub.3).sub.2                                                                                      "                    "          H           2-CH.sub.2 OH                                                                              "         N(CH.sub.3)C.sub.2 H.sub.4                                                                  "                    H          6-NHCOCH.sub.3                                                                             2-CH.sub.2 Cl                                                                            C.sub.2 H.sub.5                                                                            NHC.sub.3 H.sub.6                                                                           Na                   CH.sub.3     "         3-CH(CH.sub.3).sub.2                                                                     C.sub.2 H.sub.4 OCH.sub.3                                                                  NHC.sub.2 H.sub.4                                                                           Na                   "          6-CH.sub.3  3-CH.sub.3                                                                                 "           "          Na                   "          6-C.sub.6 H.sub.11                                                                         2-CH.sub.2 OC.sub.6 H.sub.5                                                              C.sub.2 H.sub.4 SO.sub.2 NH.sub.2                                                          NHC.sub.2 H.sub.4                                                                           Na                   "          6-OC.sub.6 H.sub.5                                                                         2-CH.sub.2 OC.sub.2 H.sub.5                                                              C.sub.2 H.sub.4 N(COCH.sub.3).sub.2                                                          "          "                    CH.sub.2 Cl                                                                               6-SCH.sub.3                                                                                 ##STR15##                                                                               C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2                                             H.sub.5     NHC.sub.2 H.sub.4                                                                           K                     ##STR16## 6-SC.sub.6 H.sub.5                                                                         2-CH.sub.2 Cl                                                                            C.sub.2 H.sub.4 SO.sub.2 NH(C.sub.2                                            H.sub.5)    NHCH.sub.2CH(C.sub.6                                                           H.sub.5)     K                     ##STR17## 6-NHCOOCH.sub.3                                                                            2-CH.sub.2 OH                                                                            C.sub.2 H.sub.4 OH                                                                         OC.sub.2 H.sub.4                                                                            Na                   H          6-NHSO.sub.2 CH.sub.3                                                                        "       C.sub.2 H.sub.4 CN                                                                         NHC.sub.2 H.sub.4 OC.sub.2                                                     H.sub.4      Na                   H          8-OCH.sub.3, 5-NHCOCH.sub.3                                                                 ##STR18##                                                                               C.sub.2 H.sub.4 OCOCH.sub.3                                                                NHC.sub.2 H.sub.4                                                                           NH.sub.4             H          6-NHCOCH.sub.2 Cl                                                                            "       C.sub.6 H.sub.13                                                                           OC.sub.2 H.sub.4                                                                            K                    H          6-NHCOC.sub.2 H.sub.4 OH                                                                   3-C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.4 OH                                                                         OC.sub.2 H.sub.4                                                                            K                    H          8-CH.sub.3, 5-Cl                                                                             "       CH.sub.2 C.sub.6 H.sub.5                                                                   NHC.sub.3 H.sub.6                                                                           K                    C.sub.6 H.sub.4p-C.sub.6 H.sub.11                                                         6-NHCONHC.sub.2 H.sub.5                                                                    2-CH.sub.2 OC.sub.6 H.sub.5                                                              C.sub.2 H.sub.4 CN                                                                         OC.sub.2 H.sub.4                                                                            NH.sub.4             C.sub.6 H.sub.4p-C.sub.2 H.sub.5                                                          6-NHCON(C.sub.2 H.sub.5).sub.2                                                             2-CH.sub.2 OC.sub.6 H.sub.5                                                              C.sub.2 H.sub.5                                                                            NHC.sub.2 H.sub.4                                                                           K                    C.sub.6 H.sub.4p-OCH.sub. 3                                                               6-OC.sub.6 H.sub.5                                                                         H         C.sub.2 H.sub.4 NHCOCH.sub.3                                                                 "          "                    C.sub.6 H.sub.4p-SCN                                                                      6-NHCOCH.sub.3                                                                             "         C.sub.2 H.sub.4 CONH.sub.2                                                                   "          "                    C.sub.6 H.sub.4p-SC.sub.2 H.sub.5                                                         H           "         C.sub.2 H.sub.4 NHCOCH.sub.3                                                               N(C.sub.6 H.sub.5)C.sub.2                                                      H.sub.4      Na                   __________________________________________________________________________

                                      TABLE 4                                      __________________________________________________________________________      ##STR19##                                                                     R.sup.1    R.sup.9  R.sup.2   R.sup.4  X'Z         M                           __________________________________________________________________________     H          C.sub.6 H.sub.5                                                                         H         CH.sub.3 NHC.sub.2 H.sub.4                                                                          Na                          H          CH.sub.3 6-CH.sub.3                                                                               CH.sub.3 "           "                           H          "        "         C.sub.6 H.sub.5                                                                         "           "                           H          "        H         C.sub.2 H.sub.5                                                                         "           "                           C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.5                                                                         H         H        "           "                           "          "        "         CH.sub.3 "           "                           "          CH.sub.3 "         CH.sub.3 N(CH.sub.3)C.sub.2 H.sub.4                                                                 "                           H          "        5-OC.sub.2 H.sub.5                                                                       "        NHC.sub.3 H.sub.6                                                                          "                           CH.sub.3   CH.sub.3 "         H        NHC.sub.2 H.sub.4                                                                          "                           "          C.sub.6 H.sub.4p-Br                                                                     H         H        "           "                           "          C.sub.6 H.sub.5                                                                         "         C.sub.2 H.sub.4 CONH.sub.2                                                              "           K                           "          C.sub.6 H.sub.4p-OCH.sub.3                                                              "         C.sub.2 H.sub.4 CN                                                                      N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          K                           CH.sub.2 Cl                                                                               "        5-C.sub.6 H.sub.11                                                                       C.sub.2 H.sub.4 SO.sub.2 NH.sub.2                                                       NHC.sub.2 H.sub.4                                                                          "                            ##STR20## C.sub.2 H.sub.4 CN                                                                      6-OC.sub.6 H.sub.5                                                                       C.sub.2 H.sub.4 N(COCH.sub.3).sub.2                                                     "           "                            ##STR21## C.sub.2 H.sub.4 OCOCH.sub.3                                                             6-SCH.sub.3                                                                              C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5                                              NHC.sub.2 H.sub.4                                                                          K                           H          CH.sub.3 6-SC.sub.6 H.sub.5                                                                       C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5                                              NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              K                           H          "        6-NHCOOCH.sub.3                                                                          C.sub.2 H.sub.4 OH                                                                      OC.sub.2 H.sub.4                                                                           Na                          H          C.sub.3 H.sub.7                                                                         6-NHSO.sub.2 CH.sub.3                                                                    C.sub.2 H.sub.4 CN                                                                      NHC.sub.2 H.sub.4 OC.sub.2                                                                 Nasub.4                     H          CH.sub.3 6-OCH.sub.3                                                                              C.sub.2 H.sub.4 OCOCH.sub.3                                                             NHC.sub.2 H.sub.4                                                                          NH.sub.4                                        5-NHCOCH.sub.3                                             H          C.sub.2 H.sub.5                                                                         6-NHCOCH.sub.2 Cl                                                                        C.sub.6 H.sub.13                                                                        OC.sub.2 H.sub.4                                                                           K                           C.sub.6 H.sub.4p-C.sub.6 H.sub.11                                                         "        6-NHCOC.sub.2 H.sub.4 OH                                                                 C.sub.2 H.sub.4 OH                                                                      OC.sub.2 H.sub.4                                                                           K                           C.sub.6 H.sub.4p-C.sub.2 H.sub.5                                                          "        "         CH.sub.2 C.sub.6 H.sub.5                                                                NHC.sub.3 H.sub.6                                                                          K                           C.sub.6 H.sub.4p-OCH.sub.3                                                                C.sub.2 H.sub.5                                                                         6-NHCONHC.sub.2 H.sub.5                                                                  C.sub.2 H.sub.4 CN                                                                      OC.sub.2 H.sub.4                                                                           NH.sub.4                    C.sub.6 H.sub.4p-SCN                                                                      C.sub.6 H.sub.4p-OCH.sub.3                                                              6-NHCON(C.sub.2 H.sub.5).sub.2                                                           C.sub.2 H.sub.5                                                                         NHC.sub.2 H.sub.4                                                                          K                           C.sub.6 H.sub.4p-SC.sub.2 H.sub.5                                                         C.sub.2 H.sub.5                                                                         6-CH.sub.3                                                                               C.sub.2 H.sub.4 NHCOCH.sub.3                                                            "           "                           C.sub.6 H.sub.4p-CONH.sub.2                                                               C.sub.2 H.sub.5                                                                         6-NHCOCH.sub.3                                                                           C.sub.2 H.sub.4 CONH.sub.2                                                              "           "                           C.sub.6 H.sub.4p-CH.sub.3                                                                 CH.sub.3 H         C.sub.2 H.sub.4 NHCOCH.sub.3                                                            "           Na                          C.sub.6 H.sub.5o-CONHCH.sub.3                                                             "        "         C.sub.2 H.sub.4 Cl                                                                      "           "                           C.sub.6 H.sub.5o-C.sub.6 H.sub.11                                                         C.sub.6 H.sub.4p-CH.sub.3                                                               6-OH      "        "           "                           __________________________________________________________________________

                                      TABLE 5                                      __________________________________________________________________________      ##STR22##                                                                     R.sup.1    R.sup.9 R.sup.10 X'Z         M                                      __________________________________________________________________________     H          C.sub.6 H.sub.5                                                                        H        NHC.sub.2 H.sub.4                                                                          Na                                     H          CH.sub.3                                                                               "        OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                          Na                                     H          CH.sub.3                                                                               H        OC.sub.2 H.sub.4                                                                           Na                                     H          CH.sub.3                                                                               C.sub.6 H.sub.5                                                                         NHC.sub.2 H.sub.4                                                                          Na                                     C.sub.6 H.sub.5                                                                           CH.sub.3                                                                               C.sub.6 H.sub.5                                                                         NHC.sub.3 H.sub.6                                                                          Na                                     "          C.sub.6 H.sub.5                                                                        CH.sub.3 NHC.sub.2 H.sub.4                                                                          Na                                     "          C.sub.6 H.sub.5                                                                        "        "           NH.sub.4                               H          "       "        N(C.sub.2 H.sub.5)C.sub.2 H.sub.4                                                          "                                      CH.sub.3   CH.sub.3                                                                               H        NHC.sub.2 H.sub.4                                                                          K                                      "          "       H        NH(CH.sub.2).sub.5                                                                         K                                      "          C.sub.6 H.sub.4p-Br                                                                    "        OC.sub.2 H.sub.4                                                                           K                                      "          C.sub.6 H.sub.4p-OCH.sub.3                                                             "        OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                          K                                      CH.sub.2 Cl                                                                               "       Br       NHC.sub.2 H.sub.4                                                                          K                                       ##STR23## C.sub.2 H.sub.4 CN                                                                     Br       N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          K                                       ##STR24## C.sub.2 H.sub.4 OCOCH.sub.3                                                            Br       NHC.sub.2 H.sub.4                                                                          K                                      H          CH.sub.3                                                                               C.sub.2 H.sub.5                                                                         NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              K                                      H          "       C.sub.2 H.sub.5                                                                         OC.sub.2 H.sub.4                                                                           K                                      H          C.sub.3 H.sub.7                                                                        C.sub.6 H.sub.5                                                                         NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         K                                      H          CH.sub.3                                                                               "        NHC.sub.2 H.sub.4                                                                          K                                      H          C.sub.2 H.sub.5                                                                        C.sub.6 H.sub. 4p-CH.sub.3                                                              OC.sub.2 H.sub.4                                                                           K                                      C.sub.6 H.sub.4p-C.sub.6 H.sub.11                                                         "       H        OC.sub.2 H.sub.4                                                                           K                                      C.sub.6 H.sub.4p-C.sub.2 H.sub.5                                                          "       CONHC.sub.2 H.sub.5                                                                     NHC.sub.3 H.sub.6                                                                          K                                      C.sub.6 H.sub.4p-OCH.sub.3                                                                C.sub.2 H.sub.5                                                                        CH.sub.3 OC.sub.2 H.sub.4                                                                           K                                      C.sub.6 H.sub.4p-SCN                                                                      C.sub.6 H.sub.4p-OCH.sub.3                                                             C.sub.2 H.sub.5                                                                         NHC.sub.2 H.sub.4                                                                          K                                      C.sub.6 H.sub.4p-SC.sub.2 H.sub.5                                                         C.sub.2 H.sub.5                                                                        SCN      "           K                                      C.sub.6 H.sub.4p-CONH.sub.2                                                               C.sub.2 H.sub.5                                                                        CONH.sub.2                                                                              "           K                                      C.sub.6 H.sub.4p-CH.sub.3                                                                 CH.sub.3                                                                               CH(CH.sub.3).sub.2                                                                      "           K                                      C.sub.6 H.sub.4o-CONHCH.sub.3                                                             "       C.sub.6 H.sub.5                                                                         "           K                                      C.sub.6 H.sub.4o-C.sub.6 H.sub.11                                                         C.sub.6 H.sub.4p-CH.sub.3                                                              C.sub.2 H.sub.5                                                                         NHC.sub.2 H.sub.4 OCH.sub.2                                                                K                                      __________________________________________________________________________

                                      TABLE 6                                      __________________________________________________________________________      ##STR25##                                                                     R.sup.1  R.sup.4  R.sup.11    X'Z         M                                    __________________________________________________________________________     H        H        CH.sub.3    NHC.sub.2 H.sub.4                                                                          K                                    H        H        C.sub.6 H.sub.4p-OCH.sub.3                                                                 "           "                                    H        H        CF.sub.3    "           "                                    H        H        COOC.sub.2 H.sub.5                                                                         "           "                                    C.sub.6 H.sub.5                                                                         H                                                                                        ##STR26##  "           Na                                   "        H        C.sub.6 H.sub.5                                                                            "           K                                    "        C.sub.6 H.sub.5                                                                         C.sub.6 H.sub.4p-Br                                                                        "           "                                    H        "        C(CH.sub.3).sub.3                                                                          "           "                                    CH.sub.3 "        C.sub.6 H.sub.11                                                                           "           Na                                   "        "        C.sub.6 H.sub.5                                                                            "           Na                                   "        C.sub.6 H.sub.5 SO.sub.2                                                                CH.sub.3    N(CH.sub.3)C.sub.2 H.sub.4                                                                 Na                                   "        C.sub.2 H.sub.5 SO.sub.2                                                                "           NHC.sub.2 H.sub.4                                                                          K                                    CH.sub.2 Cl                                                                              ##STR27##                                                                              "           N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          K                                     ##STR28##                                                                               ##STR29##                                                                              CH.sub.3    NHC.sub.2 H.sub.4                                                                          K                                     ##STR30##                                                                              CH.sub.3 CONH.sub.2  NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              K                                    H        C.sub.2 H.sub.4 OH                                                                      C.sub.2 H.sub.5                                                                            OC.sub.2 H.sub.4                                                                           K                                    H        C.sub.2 H.sub.4 CN                                                                      "           NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         K                                    H        C.sub.2 H.sub.4 OCOCH.sub.3                                                             "           NHC.sub.2 H.sub.4                                                                          K                                    H        C.sub.6 H.sub.11                                                                        CF.sub.3    OC.sub.2 H.sub.4                                                                           K                                    H        C.sub.2 H.sub.4 OH                                                                      C.sub.6 H.sub.4 p-Cl                                                                       OC.sub.2 H.sub.4                                                                           K                                    C.sub.6 H.sub.4p-C.sub.6 H.sub.11                                                       CH.sub.2 C.sub.6 H.sub.5                                                                CONHC.sub.2 H.sub.5                                                                        NHC.sub.3 H.sub.6                                                                          K                                    C.sub.6 H.sub.4p-C.sub.2 H.sub.5                                                        C.sub.2 H.sub.4 CN                                                                      CH(CH.sub.3).sub.2                                                                         OC.sub.2 H.sub.4                                                                           K                                    C.sub.6 H.sub.4p-OCH.sub.3                                                              C.sub.2 H.sub.5                                                                         "           NHC.sub.2 H.sub.4                                                                          K                                    C.sub.6 H.sub.4p-SCN                                                                    C.sub.2 H.sub.4 NHCOCH.sub.3                                                            C.sub.2 H.sub.5                                                                            "           K                                    C.sub.6 H.sub.4p-SC.sub.2 H.sub.5                                                       C.sub.2 H.sub.4 CONH.sub.2                                                              CH.sub.3    "           K                                    C.sub.6 H.sub.4p-CONH.sub.2                                                             C.sub.2 H.sub.4 NHCOCH.sub.3                                                            C.sub.2 H.sub.5                                                                            "           K                                    C.sub.6 H.sub.4p-CH.sub.3                                                               "        C.sub.6 H.sub.5                                                                            "           K                                    __________________________________________________________________________

                                      TABLE 7                                      __________________________________________________________________________      ##STR31##                                                                     R.sup.1 Q  Q' R.sup.12   R.sup.13                                                                              X'Z    M                                       __________________________________________________________________________     H       CO CO C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.5                                                                       NHC.sub.2 H.sub.4                                                                     Na                                      H       CO CO CH.sub.3   CH.sub.2 OH                                                                           "      Na                                      H       CN CO --         NHCO.sub.2 C.sub.2 H.sub.5                                                            OC.sub.2 H.sub.4                                                                      Na                                      H       CN CO --         CH.sub.3                                                                              NHC.sub.2 H.sub.4                                                                     Na                                      C.sub.6 H.sub.5                                                                        CO SO.sub.2                                                                          NH.sub.2   OC.sub.6 H.sub.5                                                                      "      "                                       "       CO SO.sub.2                                                                          CH.sub.3   OCH.sub.3                                                                             "      "                                       "       CN SO.sub.2                                                                          --         C.sub.6 H.sub.5                                                                       "      "                                       H       CO CO CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2                                                              "      K                                       CH.sub.3                                                                               CO CO 1,2-C.sub.6 H.sub.4                                                                              "      K                                       "       CO CO C.sub.2 H.sub.5                                                                           OC.sub.2 H.sub.5                                                                      "      K                                       "       CO CO CF.sub.3   H      "      K                                       "       CO CO OCH.sub.3  H      "      K                                       CH.sub.2 CL                                                                            CO CO CH.sub.2 Cl                                                                               H      "      K                                        ##STR32##                                                                             CO CO "          CH.sub.3                                                                              "      K                                        ##STR33##                                                                             CO CO NHC.sub.2 H.sub.5                                                                         NH.sub.2                                                                              N(CH.sub.3)C.sub.2 H.sub.4                                                            K                                       H       CO CO NHC.sub.2 H.sub.5                                                                         NH.sub.2                                                                              C(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                     K                                       H       CO CO OC.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                       NHC.sub.2 H.sub.4                                                                     K                                       H       CO CO OCH.sub.2C.sub.6 H.sub.5                                                                  "      NHC.sub.2 H.sub.4                                                                     K                                       H       CO CO OC.sub.6 H.sub.11                                                                         OCH.sub.3                                                                             NHC.sub.2 H.sub.4                                                                     K                                       H       CO CO C.sub.6 H.sub.5                                                                           OCH.sub.3                                                                             NHC.sub.2 H.sub.4                                                                     K                                       C.sub.6 H.sub.4p-C.sub.6 H.sub.11                                                      CO CO NHCOC.sub.2 H.sub.5                                                                       NHCO.sub.2 C.sub.2 H.sub.5                                                            NHC.sub.2 H.sub.4                                                                     K                                       C.sub.6 H.sub.4p-C.sub.2 H.sub.5                                                       CO CO NHSO.sub.2 C.sub.2 H.sub.5                                                                NHCO.sub.2 C.sub.2 H.sub.5                                                            NHC.sub.2 H.sub.4                                                                     K                                       C.sub.6 H.sub.4p-OCH.sub.3                                                             CO CO NHCOC.sub.6 H.sub.5                                                                       NHCO.sub.2 C.sub.2 H.sub.5                                                            NHC.sub.2 H.sub.4                                                                     K                                       C.sub.6 H.sub.4p-SCN                                                                   CO CO OC.sub.2 H.sub.5                                                                          NHCO.sub.2 C.sub.2 H.sub.5                                                            NHC.sub.2 H.sub.4                                                                     K                                       __________________________________________________________________________

                                      TABLE 8                                      __________________________________________________________________________      ##STR34##                                                                              OH                                                                    R.sup.1  Position                                                                            R.sup.2   X'Z         M                                          __________________________________________________________________________     H        2    5-CH.sub.3                                                                               NHC.sub.2 H.sub.4                                                                          Na                                         H        2    5-CH.sub.3                                                                               OC.sub.2 H.sub.4                                                                           Na                                         H        2    5-OCH.sub.3                                                                              NHC.sub.2 H.sub.4                                                                          K                                          H        2    5-Cl      "           Na                                         C.sub.6 H.sub.5                                                                         2    5-Cl      "           Na                                         "        4    3-OCH.sub.3                                                                              "           K                                          "        4    3-OCH.sub.3                                                                              "           K                                          H        3,4  H         "           Na                                         CH.sub.3 4    2-NHC.sub.6 H.sub.5                                                                      "           Na                                         "        2    5-NHCOCH.sub.3                                                                           "           Na                                         CH.sub.3 3,4  H         N(CH.sub.3)C.sub.2 H.sub.4                                                                 K                                          "        2                                                                                    ##STR35##                                                                               NHC.sub.2 H.sub.4                                                                          K                                                        C.sub.2 H.sub.4 OSO.sub.3 K                                      CH.sub.2 Cl                                                                             2    5-C.sub.6 H.sub.11                                                                       NHC.sub.2 H.sub.4                                                                          K                                           ##STR36##                                                                              2    5-OC.sub.6 H.sub.5                                                                       N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          "                                           ##STR37##                                                                              2    5-SCH.sub.3                                                                              NHC.sub.2 H.sub.4                                                                          K                                          H        2    5-SC.sub.6 H.sub.5                                                                       NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              Na                                         H        2    5-NHCOOCH.sub.3                                                                          OC.sub.2 H.sub.4                                                                           Na                                         H        2    5-NHSO.sub.2 CH.sub.3                                                                    NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         Na                                         H        2    5-NHCOCH.sub.3                                                                           NHC.sub.2 H.sub.4                                                                          NH.sub.4                                   H        2    5-NHCOCH.sub.2 Cl                                                                        OC.sub.2 H.sub.4                                                                           K                                          C.sub.6 H.sub.4p-C.sub.6 H.sub.11                                                       2    5-NHCOC.sub.2 H.sub.4 OH                                                                 OC.sub.2 H.sub.4                                                                           K                                          C.sub.6 H.sub.4p-C.sub.2 H.sub.5                                                        2    5-Cl      NHC.sub.3 H.sub.6                                                                          K                                          C.sub.6 H.sub.4p-OCH.sub.3                                                              2    5-NHCONC.sub.2 H.sub.5                                                                   OC.sub.2 H.sub.4                                                                           NH.sub.4                                   C.sub.6 H.sub.4p-SCN                                                                    2    5-NHCON(C.sub.2 H.sub.5).sub. 2                                                          NHC.sub.2 H.sub.4                                                                          K                                          C.sub.6 H.sub.4p-SC.sub.2 H.sub.5                                                       2    5-CH.sub.3                                                                               "           "                                          C.sub.6 H.sub.4p-CONH.sub.2                                                             2    5-NHCOCH.sub.3                                                                           "           "                                          C.sub.6 H.sub.4p-CH.sub.3                                                               4    H         "           Na                                         __________________________________________________________________________

                                      TABLE 9                                      __________________________________________________________________________      ##STR38##                                                                              OH                                                                    R.sup.1  Position                                                                            R.sup.2         R.sup.14                                                                               X'Z         M                            __________________________________________________________________________     H        2    H               6-SO.sub.2 N(CH.sub.3).sub.2                                                           NHC.sub.2 H.sub.4                                                                          Ma                           H        2    H               "       "           "                            H        2    3-CONH.sub.2    H       "           Na                           H        4    H               H       N(CH.sub.3)C.sub.2 H.sub.4                                                                 "                            C.sub.6 H.sub.5                                                                         4    H               H       OC.sub.2 H.sub.4                                                                           K                            "        2,6  H               H       OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                          K                            "        2    H               H       OC.sub.2 H.sub.4                                                                           K                            H        "    H               6-SO.sub.2 NHCH.sub.3                                                                  OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                          K                            CH.sub.3 2    3-CONH.sub.2    H       NHC.sub.2 H.sub.4                                                                          Na                           "        2    3-CONHC.sub.6 H.sub.5                                                                          H       NHCH(C.sub.2 H.sub.5)CH.sub.2                                                              Na                           "        2    3-CONHC.sub.6 H.sub.4p-OC.sub.2 H.sub.4 OH                                                     H       OC.sub.2 H.sub.4                                                                           NH.sub.4                     "        4    H               H       NHC.sub.2 H.sub.4                                                                          Na                           CH.sub.2 Cl                                                                             4    H               H       NHC.sub.2 H.sub.4                                                                          Na                            ##STR39##                                                                              4    H               H       "           "                             ##STR40##                                                                              2    H               H       NHC.sub.2 H.sub.4                                                                          K                            H        2    "               "       NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              K                            H        2    3-CO.sub.2 CH.sub.3                                                                            "       OC.sub.2 H.sub.4                                                                           Na                           H        2    "               "       NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         Na                           H        2,4  H               H       NHC.sub.2 H.sub.4                                                                          NH.sub.4                     H        2    3-COCH.sub.2 Cl "       OC.sub.2 H.sub.4                                                                           K                            C.sub.6 H.sub.4p-C.sub.6 H.sub.11                                                       4    H               "       OC.sub.2 H.sub.4                                                                           K                            C.sub.6 H.sub.4p-C.sub.2 H.sub.5                                                        4    H               H       NHC.sub.3 H.sub.6                                                                          K                            C.sub.6 H.sub.4p-OCH.sub.3                                                              4    H               "       OC.sub.2 H.sub.4                                                                           NH.sub.4                     C.sub.6 H.sub.4p-SCN                                                                    4    H               "       NHC.sub.2 H.sub.4                                                                          K                            C.sub.6 H.sub.4p-SC.sub.2 H.sub.5                                                       4    H               "       "           "                            C.sub.6 H.sub.4p-CONH.sub.2                                                             2    3-CONHC.sub.6 H.sub.5                                                                          "       "           "                            C.sub.6 H.sub.4p-CH.sub.3                                                               2    H               "       N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          "                            __________________________________________________________________________

                                      TABLE 10                                     __________________________________________________________________________      ##STR41##                                                                     R.sup.1  R.sup.16      R.sup.17                                                                             R.sup.2                                                                             R.sup.14                                                                            X'Z         M                           __________________________________________________________________________     H        C.sub.6 H.sub.11                                                                             H     H    H    NHC.sub.2 H.sub.4                                                                          Na                          H        C.sub.2 H.sub.4 CONH.sub.2                                                                   H     H    "    "           "                           H        C.sub.2 H.sub.4 SO.sub.2 CHCH.sub.2                                                          H     H    8-OH "           Na                          H        C.sub.2 H.sub.4 NHSO.sub.2 CH.sub.3                                                          H     H    H    N(CH.sub.3)C.sub.2 H.sub.4                                                                 "                           C.sub.6 H.sub.5                                                                          ##STR42##    H     3-OCH.sub.3                                                                         8-OH OC.sub.2 H.sub.4                                                                           K                           "        C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3                                                   H     H    H    OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                          K                           "        CH(CH.sub.3)C.sub.2 H.sub.5                                                                  H     H    H    OC.sub.2 H.sub.4                                                                           K                           H        CH(CH.sub.3)CH.sub.2 CH(CH.sub.3)CH.sub.3                                                    CH.sub.3                                                                             H    H    OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                          K                           CH.sub.3 C.sub.6 H.sub.5                                                                              H     3-OCH.sub.3                                                                         H    NHC.sub.2 H.sub.4                                                                          Na                          "        C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.4 OH                                                                   "    H    NHCH(C.sub.2 H.sub.5)CH.sub.2                                                              Na                          "        CH.sub.2 CH(OH)CH.sub.2 OH                                                                   "     H    H    OC.sub.2 H.sub.4                                                                           NH.sub.4                    "        C.sub.2 H.sub.4 SO.sub.2 NH.sub.2                                                            H     H    H    NHC.sub.2 H.sub.4                                                                          Na                          CH.sub.2 Cl                                                                             (CH.sub.2).sub.3 NHCOCH.sub.3                                                                H     H    H    NHC.sub.2 H.sub.4                                                                          Na                           ##STR43##                                                                              C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                          H     H    H    "           "                            ##STR44##                                                                              C.sub.3 H.sub.6 OCH.sub.3                                                                    H     H    H    NHC.sub.2 H.sub.4                                                                          K                           H        CH.sub.2 C.sub.6 H.sub.5                                                                     CH.sub.2 C.sub.6 H.sub.5                                                             "    "    NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              K                           H        C.sub.6 H.sub.11                                                                             H     H    "    OC.sub.2 H.sub.4                                                                           Na                          H        C.sub.2 H.sub.4 CONH.sub.2                                                                   H     "    "    NHC.sub.2 H.sub.4 OC.sub.2                                                                 Nasub.4                     H        C.sub.2 H.sub.4 SO.sub.2 CHCH.sub.2                                                          H     H    8-OCH.sub.3                                                                         NHC.sub.2 H.sub.4                                                                          NH.sub.4                              ##STR45##    H     3-OC.sub.2 H.sub.5                                                                  8-OC.sub.2 H.sub.5                                                                  OC.sub.2 H.sub.4                                                                           K                           C.sub.6 H.sub.4p-C.sub.6 H.sub.11                                                        ##STR46##    H     H    "    OC.sub.2 H.sub.4                                                                           K                           C.sub.6 H.sub.4p-C.sub.2 H.sub.5                                                        C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3                                                   H     H    H    NHC.sub.3 H.sub.6                                                                          K                           C.sub.6 H.sub.4p-OCH.sub.3                                                              CH(CH.sub.3)C.sub.2 H.sub.5                                                                  H     H    "    OC.sub.2 H.sub.4                                                                           NH.sub.4                    C.sub.6 H.sub.4p-SCN                                                                    CH(CH.sub.3)CH.sub.2 CH(CH.sub.3)CH.sub.3                                                    H     H    "    NHC.sub.2 H.sub.4                                                                          K                           C.sub.6 H.sub.4p-SC.sub.2 H.sub.5                                                       C.sub.6 H.sub.5                                                                              H     3-C.sub.2 H.sub.5                                                                   "    "           "                           C.sub.6 H.sub.4p-CONH.sub.2                                                             C.sub.2 H.sub.5                                                                              "     H    "    "           "                           C.sub.6 H.sub.4p-CH.sub.3                                                               CH.sub.2 CH(OH)CH.sub.2 OH                                                                   "     H    "    N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          "                           __________________________________________________________________________

                                      TABLE 11                                     __________________________________________________________________________      ##STR47##                                                                     R        R.sup.2   R.sup.4  R.sup.5   X'Z            M                         __________________________________________________________________________     H        H         C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 NHCOCH.sub.3                                                             NHC.sub.2 H.sub.4                                                                             Na                        H        H         C.sub.2 H.sub.5                                                                         C.sub.3 H.sub.7n                                                                         N(CH.sub.3)C.sub.2 H.sub.4                                                                    "                         H        H         "        C.sub.2 H.sub.5                                                                          NHCH.sub.2CH(OSO.sub.2 Na)CH.sub.2                                                            Na                        H        H         CH.sub.3 C.sub.2 H.sub.4 SO.sub.2 CHCH.sub.2                                                      "              "                         H        H         C.sub.2 H.sub.4 OH                                                                      C.sub.2 H.sub.4 CN                                                                       OC.sub.2 H.sub.4                                                                              K                         H        3-CH.sub.3                                                                               C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 CN                                                                       OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                             Na                        CH.sub. 3                                                                               3-CH.sub.3                                                                               C.sub.2 H.sub.4 OH                                                                      C.sub.2 H.sub.4 OH                                                                       OC.sub.2 H.sub.4                                                                              Na                        SO.sub.2 CH.sub.3                                                                       2-CH.sub.33-Cl                                                                           H        CH.sub.2 C.sub.6 H.sub.5                                                                 NHC.sub.3 H.sub.6                                                                             K                         Cl       3-Cl      C.sub.6 H.sub.11                                                                        C.sub.2 H.sub.4 OSO.sub.3 K                                                              "              K                         C.sub.6 H.sub.5                                                                         3-NHCOCH.sub.3                                                                           C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 CN                                                                       NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                            Na                        Br       "         "        C.sub.2 H.sub.4 CONH.sub.2                                                               NHC.sub.2 H.sub.4                                                                             K                         C.sub.2 H.sub.5                                                                         2-CH.sub.3                                                                               H        C.sub.2 H.sub.4 SO.sub.2 NH.sub.2                                                        NHC.sub.2 H.sub.4                                                                             Na                        C.sub.6 H.sub.4o-OCH.sub.3                                                              2-OC.sub.6 H.sub.5                                                                       C.sub.2 H.sub.4 CN                                                                      C.sub.2 H.sub.4 N(COCH.sub.3).sub.2                                                      N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                             "                         C.sub.6 H.sub.4o-Cl                                                                     3-SCH.sub.3                                                                              C.sub.2 H.sub.4 OCOCH.sub.3                                                             C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5                                               NHC.sub.2 H.sub.4                                                                             K                         C.sub.6 H.sub.4o-CH.sub.3                                                               3-CH.sub.3                                                                               C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 OCOCH.sub.3                                                              NHC.sub.2 H.sub. 4 OC.sub.2                                                                   Nasub.4                   C.sub.6 H.sub.4o-C.sub.2 H.sub.5                                                        3-SC.sub.6 H.sub.5 C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5                                               NHCH.sub.2CH(C.sub.6 H.sub.5)                                                                 K                         C.sub.6 H.sub.4o-Br                                                                     3-NHCOOCH.sub. 3                                                                         C.sub.2 H.sub.4 OH                                                                      C.sub.2 H.sub.4 OH                                                                       OC.sub. 2 H.sub.4                                                                             Na                        C.sub.6 H.sub.4o-OC.sub.2 H.sub.5                                                       3-NHSO.sub.2 CH.sub.3                                                                    C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 CN                                                                       NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                            Na                        C.sub.6 H.sub.4m-CH.sub.3                                                               2-OCH.sub.3,                                                                             C.sub.2 H.sub.4 OCOCH.sub.3                                                             C.sub.2 H.sub.4 OCOCH.sub.3                                                              NHC.sub.2 H.sub.4                                                                             NH.sub.4                  C.sub.6 H.sub.4m-C.sub.2 H.sub.5                                                        3-NHCOCH.sub.2 Cl                                                                        C.sub.2 H.sub.4 OH                                                                      C.sub.6 H.sub.13                                                                         OC.sub.2 H.sub.4                                                                              K                         C.sub.6 H.sub.4m-Cl                                                                     3-NHCOC.sub.2 H.sub.4 OH                                                                 H        C.sub.2 H.sub.4 OH                                                                       OC.sub.2 H.sub.4                                                                              K                         H        2-CH.sub.3, 3-Cl                                                                         H        CH.sub.2 C.sub.6 H.sub.5                                                                 NHC.sub.3 H.sub.6                                                                             K                         H        2-NHCONHC.sub.2 H.sub.5                                                                  C.sub.2 H.sub.4 OH                                                                      C.sub.2 H.sub.4 CN                                                                       OC.sub.2 H.sub. 4                                                                             NH.sub.4                  H        2-NHCON(C.sub.2 H.sub.5).sub.2                                                           C.sub.2 H.sub.4 OSO.sub.3 K                                                             C.sub.2 H.sub.5                                                                          NHC.sub.2 H.sub.4                                                                             K                         H        3-CH.sub.3                                                                               C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 NHCOCH.sub.3                                                             "              "                         H        3-NHCOCH.sub.3                                                                           "        C.sub.2 H.sub.4 CONH.sub.2                                                               "              "                         H        H         "        C.sub.2 H.sub.4 NHCOCH.sub.3                                                             "              Na                        C.sub.6 H.sub.4p-CH.sub.3                                                               H         CH.sub.2 CH.sub.2OCH.sub.2 CH.sub.2                                                               "              Na                        C.sub.6 H.sub.4p-OCH.sub.3                                                              H         CH.sub.2 CH.sub.2SCH.sub.2 CH.sub.2                                                               "              Na                        C.sub.6 H.sub.4p-Cl                                                                     H         CH.sub.2 CH.sub.2SO.sub.2CH.sub.2 CH.sub.2                                                        "              Na                        C.sub.6 H.sub.4p-Br                                                                     H         CH.sub.2 CH.sub.2NHCH.sub.2 CH.sub.2                                                              "              Na                        H        H         CH.sub.2 CH.sub.2N(COCH).sub.3 CH.sub.2 CH.sub.2                                                  "              Na                        __________________________________________________________________________

                                      TABLE 12                                     __________________________________________________________________________      ##STR48##                                                                     R        R.sup.2   R.sup.8 R.sup.4  X'Z         M                              __________________________________________________________________________     H        7-CH.sub.3                                                                               2-CH.sub.3                                                                             C.sub.2 H.sub.5                                                                         NHC.sub.2 H.sub.4                                                                          K                              H        "         "       "        N(C.sub.2 H.sub.5)C.sub.2 H.sub.4                                                          "                              H        H         2,2,4-(CH.sub.3).sub.3                                                                 C.sub.2 H.sub.5                                                                         NHC.sub.3 H.sub.6                                                                          Na                             H        H         "       C.sub.2 H.sub.4 OSO.sub.3 Na                                                            OC.sub.2 H.sub.4                                                                           Na                             H        H         "       "        NHC.sub.2 H.sub.4                                                                          Na                             H        7-CH.sub.3                                                                               2-CH.sub.3                                                                             C.sub.2 H.sub.4 NHCOCH.sub.3                                                            "           "                              CH.sub.3 7-NHCOCH.sub.3                                                                           H       C.sub.2 H.sub.4 OH                                                                      OC.sub.2 H.sub.4                                                                           K                              SO.sub.2 CH.sub.3                                                                       "         "       C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                        NHC.sub.2 H.sub.4                                                                          Na                             Cl       5-CH.sub.3                                                                               "       "        "           K                              C.sub.6 H.sub.5                                                                         8-CH.sub.3                                                                               "       C.sub.2 H.sub.4 OCH.sub.3                                                               N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          NH.sub.4                       Br       7-CH.sub.3                                                                               2,2,4-(CH.sub.3).sub.3                                                                 C.sub.2 H.sub.5                                                                         NHC.sub.2 H.sub.4                                                                          K                              C.sub.2 H.sub.5                                                                         "         "       C.sub.2 H.sub.4 Cl                                                                      NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         K                              C.sub.6 H.sub.4o-OCH.sub.3                                                              "         "       "        NHC.sub.2 H.sub.4                                                                          K                              C.sub.6 H.sub.4o-Cl                                                                     7-SC.sub.6 H.sub.5                                                                       "       C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5                                              NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              K                              C.sub.6 H.sub.4o-CH.sub.3                                                               7-NHCOOCH.sub.3                                                                          CH.sub.3                                                                               C.sub.2 H.sub.4 OH                                                                      OC.sub.2 H.sub.4                                                                           Na                             C.sub.6 H.sub.4o-C.sub.2 H.sub.5                                                        7-NHSO.sub.2 CH.sub.3                                                                    2-C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.4 CN                                                                      NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         Na                             C.sub.6 H.sub.4o-Br                                                                     7-OCH.sub.3,                                                                             3-OCOCH.sub.3                                                                          C.sub.2 H.sub.4 OCOCH.sub.3                                                             NHC.sub.2 H.sub.4                                                                          NH.sub.4                                5-NHCOCH.sub.3                                                        C.sub.6 H.sub.4m-CH.sub.3                                                               7-NHCOCH.sub.2 Cl                                                                        3-OH    C.sub.6 H.sub.13                                                                        OC.sub.2 H.sub.4                                                                           K                              C.sub.6 H.sub.4m-OCH.sub.3                                                              7-NHCOC.sub.2 H.sub.4 OH                                                                 3-CONH.sub.2                                                                           C.sub.2 H.sub.4 OH                                                                      OC.sub.2 H.sub.4                                                                           K                              C.sub.6 H.sub.4m-C.sub.2 H.sub.5                                                        7-CH.sub.3, 3-Cl                                                                         3-Cl    CH.sub.2 C.sub.6 H.sub.5                                                                NHC.sub.3 H.sub.6                                                                          K                              C.sub.6 H.sub.4m-Cl                                                                     7-NHCONHC.sub.2 H.sub.5                                                                  3-OC.sub.6 H.sub.5                                                                     C.sub.2 H.sub.4 CN                                                                      OC.sub.2 H.sub.4                                                                           NH.sub.4                       H        7-NHCON(C.sub.2 H.sub.5).sub.2                                                           "       C.sub.2 H.sub.5                                                                         NHC.sub.2 H.sub.4                                                                          K                              H        7-CH.sub.3                                                                               3-SC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.4 NHCOCH.sub.3                                                            "           "                              H        7-NHCOCH.sub.3                                                                           3-CONHC.sub.2 H.sub.5                                                                  C.sub.2 H.sub.4 CONH.sub.2                                                              "           "                              H        H         3-OCH.sub.3                                                                            C.sub.2 H.sub.4 NHCOCH.sub.3                                                            "           Na                             __________________________________________________________________________

                                      TABLE 13                                     __________________________________________________________________________      ##STR49##                                                                     R        R.sup.2    R.sup.8 R.sup.4  X'Z     M                                 __________________________________________________________________________     H        H          H       CH(CH.sub.3).sub.2                                                                      NHC.sub.2 H.sub.4                                                                      K                                 H        H          H       "        OC.sub.2 H.sub.4                                                                       K                                 H        6-CH.sub.3 3-CH.sub.3                                                                             C.sub.2 H.sub.5                                                                         "       Na                                H        "          "       C.sub.2 H.sub.4 OH                                                                      "       "                                 H        "          "       C.sub.2 H.sub.4 SO.sub.2 NH.sub.2                                                       NHC.sub.2 H.sub.4                                                                      Na                                H        "          "       "        OC.sub.2 H.sub.4 OH                                                                    K                                 CH.sub.3 "          "       C.sub.2 H.sub.4 OCH.sub.3                                                               NHC.sub.2 H.sub.4                                                                      K                                 SO.sub.2 CH.sub.3                                                                       6-NHCOCH.sub.3                                                                            H       C.sub.2 H.sub.5                                                                         NHC.sub.3 H.sub.6                                                                      K                                 Cl       "          3-CH.sub.3                                                                             "        NHC.sub.2 H.sub.4                                                                      K                                 C.sub.6 H.sub.5                                                                         "          3-CH(CH.sub.3).sub.2                                                                   C.sub.2 H.sub.4 OCH.sub.3                                                               NHC.sub.2 H.sub.4                                                                      Na                                Br       "          "       C.sub.2 H.sub.4 OSO.sub.3 K                                                             N(CH.sub.3)C.sub.2 H.sub.4                                                             K                                 C.sub.2 H.sub.5                                                                         "          "       C.sub.2 H.sub.4 OH                                                                      OC.sub.2 H.sub.4                                                                       K                                 C.sub.6 H.sub.4o-OCH.sub.3                                                              "          "       C.sub.2 H.sub.4 OH                                                                      N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                      "                                 C.sub.6 H.sub.4o-Cl                                                                     6-NHCOOCH.sub.3                                                                           2-CH.sub.2 OH                                                                          C.sub.2 H.sub.4 OH                                                                      OC.sub.2 H.sub.4                                                                       Na                                C.sub.6 H.sub.4o-CH.sub.3                                                               6-NHSO.sub.2 CH.sub.3                                                                     "       C.sub.2 H.sub.4 CN                                                                      NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                     Na                                C.sub.6 H.sub.4o-C.sub.2 H.sub.5                                                        5-OCH.sub.3, 8-NHCOCH.sub.3                                                               "       C.sub.2 H.sub.4 OCOCH.sub.3                                                             NHC.sub.2 H.sub.4                                                                      NH.sub.4                          C.sub.6 H.sub.4o-OC.sub.2 H.sub.5                                                       6-NHCOCH.sub. 2 Cl                                                                        2-CH.sub.2 CH                                                                          C.sub.6 H.sub.13                                                                        OC.sub.2 H.sub.4                                                                       K                                 C.sub.6 H.sub.4m-CH.sub.3                                                               6-NHCOC.sub.2 H.sub.4 OH                                                                  H       C.sub.2 H.sub.4 OH                                                                      OC.sub.2 H.sub.4                                                                       K                                 C.sub.6 H.sub.4m-OCH.sub.3                                                              5-CH.sub.3, 8-Cl                                                                          2-CH.sub.2 Cl                                                                          CH.sub.2 C.sub.6 H.sub.5                                                                NHC.sub.3 H.sub.6                                                                      K                                 C.sub.6 H.sub.4m-C.sub.2 H.sub.5                                                        6-NHCONHC.sub.2 H.sub.5                                                                   2-CH.sub.2 Cl                                                                          C.sub.2 H.sub.4 CN                                                                      OC.sub.2 H.sub.4                                                                       NH.sub.4                          C.sub.6 H.sub.4m-Cl                                                                     6-NHCON(C.sub.2 H.sub.5).sub.2                                                            2-CH.sub.2 OC.sub.6 H.sub.5                                                            C.sub.2 H.sub.5                                                                         NHC.sub.2 H.sub.4                                                                      K                                 H        6-CH.sub.3 "       C.sub.2 H.sub.4 NHCOCH.sub.3                                                            "       "                                 H        6-NHCOCH.sub.3                                                                            2-C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                     C.sub.2 H.sub.4 CONH.sub.2                                                              "       "                                 H        H          "       C.sub.2 H.sub.4 NHCOCH.sub.3                                                            N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                      Na                                __________________________________________________________________________

                                      TABLE 14                                     __________________________________________________________________________      ##STR50##                                                                     R        R.sup.9 R.sup.2    R.sup.4  X'Z         M                             __________________________________________________________________________     H        C.sub.6 H.sub.5                                                                        H          H        NHC.sub.2 H.sub.4                                                                          Na                            H        "       "          CH.sub.3 "           Na                            H        CH.sub.3                                                                               "          C.sub.2 H.sub.4 OH                                                                      NHC.sub.2 H.sub.4                                                                          Na                            H        CH.sub.3                                                                               "          "        OC.sub.2 H.sub.4                                                                           Na                            H        "       5-CH.sub.3 "        NHC.sub.2 H.sub.4                                                                          K                             H        C.sub.6 H.sub.5                                                                        5-Cl       H        "           "                             CH.sub.3 C.sub.6 H.sub.5                                                                        5-NHCOCH.sub.3                                                                            C.sub.2 H.sub.4 CN                                                                      "           "                             SO.sub.2 CH.sub.3                                                                       "       5-OCH.sub.3                                                                               CH.sub.3 "           "                             Cl       "       H          "        "           Na                            C.sub.6 H.sub.5                                                                         "       H          "        N(C.sub.2 H.sub.5)C.sub.2 H.sub.4                                                          Na                            Br       "       H          "        N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          Na                            C.sub.2 H.sub.5                                                                         C.sub.6 H.sub.5                                                                        H          C.sub.2 H.sub.5                                                                         NHC.sub.2 H.sub.4                                                                          Na                            C.sub.6 H.sub.4o-OCH.sub.3                                                              C.sub.6 H.sub.5                                                                        H          CH.sub.3 NHC.sub.2 H.sub.4                                                                          Na                            C.sub.6 H.sub.4o-Cl                                                                     CH.sub.3                                                                               6-CH.sub.3 CH.sub.3 "           "                             C.sub.6 H.sub.4o-CH.sub.3                                                               CF.sub.3                                                                               "          C.sub.6 H.sub.5                                                                         "           "                             C.sub.6 H.sub.4o-C.sub.2 H.sub.5                                                        C.sub.6 H.sub.5                                                                        H          C.sub.2 H.sub.5                                                                         "           "                             C.sub.6 H.sub.4o-Br                                                                     C.sub.6 H.sub.5                                                                        H          H        "           "                             C.sub.6 H.sub.4o-OC.sub.2 H.sub.5                                                       CONH.sub.2                                                                             "          CH.sub.3 "           "                             C.sub.6 H.sub.4m-CH.sub.3                                                               CH.sub.3                                                                               "          CH.sub.3 N(CH.sub.3)C.sub.2 H.sub.4                                                                 "                             C.sub.6 H.sub.4m-OCH.sub.3                                                              Cl      5-OC.sub.2 H.sub.5                                                                        "        NHC.sub.3 H.sub.6                                                                          "                             C.sub.6 H.sub.4m-C.sub.2 H.sub.5                                                        CH.sub.3                                                                               "          H        NHC.sub.2 H.sub.4                                                                          "                             C.sub.6 H.sub.4m-Cl                                                                     C.sub.6 H.sub.4p-Br                                                                    H          H        "           "                             H        C.sub.6 H.sub.5                                                                        "          C.sub.2 H.sub.4 CONH.sub.2                                                              "           K                             H        C.sub.6 H.sub.4p-OCH.sub.3                                                             "          C.sub.2 H.sub.4 CN                                                                      N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          K                             H        "       6-C.sub.6 H.sub.11                                                                        C.sub.2 H.sub.4 SO.sub.2 NH.sub.2                                                       NHC.sub.2 H.sub.4                                                                          "                             H        C.sub.2 H.sub.4 CN                                                                     4-OC.sub.6 H.sub.5                                                                        C.sub.2 H.sub.4 N(COCH.sub.3).sub.2                                                     "           "                             H        C.sub.2 H.sub.4 OCOCH.sub.3                                                            5-SCH.sub.3                                                                               C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5                                              NHC.sub.2 H.sub.4                                                                          K                             H        CH.sub.3                                                                               5-SC.sub.6 H.sub.5                                                                        C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5                                              NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              K                             C.sub.6 H.sub.4p-CH.sub.3                                                               "       5-NHCOOCH.sub.3                                                                           C.sub.2 H.sub.4 OH                                                                      OC.sub.2 H.sub.4                                                                           Na                            C.sub.6 H.sub.4p-OCH.sub.3                                                              C.sub.3 H.sub.7                                                                        6-NHSO.sub.2 CH.sub.3                                                                     C.sub.2 H.sub.4 CN                                                                      NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         Na                            C.sub.6 H.sub.4p-Cl                                                                     CH.sub.3                                                                               6-OCH.sub.3, 5-NHCOCH.sub.3                                                               C.sub.2 H.sub.4 OCOCH.sub.3                                                             NHC.sub.2 H.sub.4                                                                          NH.sub.4                      C.sub.6 H.sub.4p-Br                                                                     C.sub.2 H.sub.5                                                                        6-NHCOCH.sub.2 Cl                                                                         C.sub.6 H.sub.13                                                                        OC.sub.2 H.sub.4                                                                           K                             H        OH      6-NHCOC.sub.2 H.sub.4 OH                                                                  C.sub.2 H.sub.4 OH                                                                      OC.sub.2 H.sub.4                                                                           K                             H        SO.sub.2 NH.sub.2                                                                      "          CH.sub.2 C.sub.6 H.sub.5                                                                NHC.sub.3 H.sub.6                                                                          K                             H        SO.sub.2 NHC.sub.2 H.sub.5                                                             6-NHCONHC.sub.2 H.sub.5                                                                   C.sub.2 H.sub.4 CN                                                                      OC.sub.2 H.sub.4                                                                           NH.sub.4                      H        OC.sub.6 H.sub.11                                                                      6-NHCON(C.sub.2 H.sub.5).sub.2                                                            C.sub.2 H.sub.5                                                                         NHC.sub.2 H.sub.4                                                                          K                             H        SC.sub.2 H.sub.5                                                                       6-CH.sub.3 C.sub.2 H.sub.4 NHCOCH.sub.3                                                            "           "                             H        CONHC.sub.2 H.sub.5                                                                    6-NHCOCH.sub.3                                                                            C.sub.2 H.sub.4 CONH.sub.2                                                              "           "                             CH.sub.3 OCH.sub.3                                                                              H          C.sub.2 H.sub.4 NHCOCH.sub.3                                                            "           Na                            SO.sub.2 CH.sub.3                                                                       NHOCC.sub.2 H.sub.5                                                                    "          "        "           "                             Cl       C.sub.6 H.sub.4p-CH.sub.3                                                              6-OH       "        "           "                             __________________________________________________________________________

                                      TABLE 15                                     __________________________________________________________________________      ##STR51##                                                                     R         R.sup.9 R.sup.10                                                                               X'Z         M                                        __________________________________________________________________________     H         C.sub.6 H.sub.5                                                                        H       NHC.sub.2 H.sub.4                                                                          Na                                       H         "       "       NHCH[C(CH.sub.3).sub.3 ]CH.sub.2                                                           "                                        H         "       "       OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                          "                                        H         "       CH.sub.3                                                                               "           "                                        H         CH.sub.3                                                                               C.sub.6 H.sub.5                                                                        "           "                                        H         "       "       OC.sub.2 H.sub.4                                                                           "                                        CH.sub.3  C.sub.6 H.sub.5                                                                        H       NHC.sub.2 H.sub.4                                                                          K                                        SO.sub.2 CH.sub.3                                                                        "       "       "           Na                                       Cl        "       "       "           "                                        C.sub.6 H.sub.5                                                                          "       "       "           "                                        Br        "       CH.sub.3                                                                               "           "                                        C.sub.2 H.sub.5                                                                          "       H       "           "                                        C.sub.6 H.sub.4OOCH.sub.3                                                                "       "       N(CH.sub.3)C.sub.2 H.sub.4                                                                 "                                        C.sub.6 H.sub.4OCl                                                                       "       "       N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          "                                        C.sub.6 H.sub.4OCH.sub.3                                                                 "       "       NHC.sub.2 H.sub.4                                                                          "                                        C.sub.6 H.sub.4OC.sub.2 H.sub.5                                                          CH.sub.3                                                                               "       OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                          "                                        C.sub.6 H.sub.4OBr                                                                       "       "       OC.sub.2 H.sub.4                                                                           "                                        C.sub.6 H.sub.4OOC.sub.2 H.sub.5                                                         "       C.sub.6 H.sub.5                                                                        NHC.sub.2 H.sub.4                                                                          "                                        C.sub.6 H.sub.4m-CH.sub.3                                                                "       "       NHC.sub.3 H.sub.6                                                                          "                                        C.sub.6 H.sub.4m-OCH.sub.3                                                               C.sub.6 H.sub.5                                                                        CH.sub.3                                                                               NHC.sub.2 H.sub.4                                                                          "                                        C.sub.6 H.sub.4m-C.sub.2 H.sub.5                                                         "       "       "           NH.sub.4                                 C.sub.6 H.sub.4m-Cl                                                                      "       "       N(C.sub.2 H.sub.5)C.sub.2 H.sub.4                                                          "                                        H         CH.sub.3                                                                               H       NHC.sub.2 H.sub.4                                                                          K                                        H         "       "       NH(CH.sub.2).sub.5                                                                         "                                        H         C.sub.6 H.sub.4p-Br                                                                    "       OC.sub.2 H.sub.4                                                                           "                                        H         C.sub.6 H.sub.4p-OCH.sub.3                                                             "       OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                          "                                        H         "       Br      NHC.sub.2 H.sub.4                                                                          "                                        H         C.sub.2 H.sub.4 CN                                                                     "       N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          "                                        C.sub.6 H.sub.4p-CH.sub.3                                                                C.sub.2 H.sub.4 OCOCH.sub.3                                                            "       NHC.sub.2 H.sub.4                                                                          "                                        C.sub.6 H.sub.4p-OCH.sub.3                                                               CONH.sub.2                                                                             C.sub.2 H.sub.5                                                                        NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              "                                        C.sub.6 H.sub.4p-Cl                                                                      SCN     "       OC.sub.2 H.sub.4                                                                           "                                        C.sub.6 H.sub.4p-Br                                                                      SO.sub.2 C.sub.2 H.sub.5                                                               C.sub.6 H.sub.5                                                                        NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         "                                        H         OCOCH.sub.3                                                                            C.sub.6 H.sub.4p-CH.sub.3                                                              NHC.sub.2 H.sub.4                                                                          "                                        H         CONHC.sub.2 H.sub.5                                                                    "       OC.sub.2 H.sub.4                                                                           "                                        H         OH      H       "           "                                        H         SO.sub.2 NH.sub.2                                                                      CONHC.sub.2 H.sub.5                                                                    NHC.sub.3 H.sub.6                                                                          "                                        H         SO.sub.2 NHC.sub.2 H.sub.5                                                             CH.sub.3                                                                               OC.sub.2 H.sub.4                                                                           "                                        H         OC.sub.6 H.sub.11                                                                      C.sub.2 H.sub.5                                                                        NHC.sub.2 H.sub.4                                                                          "                                        CH.sub.3  C.sub.2 H.sub.5                                                                        SCN     "           "                                        SO.sub.2 CH.sub.3                                                                        CONHC.sub.2 H.sub.5                                                                    CONH.sub.2                                                                             "           "                                        Cl        OCH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                     "           "                                        C.sub.6 H.sub.5                                                                          NHOCC.sub.2 H.sub.5                                                                    C.sub.6 H.sub.5                                                                        "           "                                        Br        "       C.sub.2 H.sub.5                                                                        "           "                                        __________________________________________________________________________

                                      TABLE 16                                     __________________________________________________________________________      ##STR52##                                                                     R         R.sup.4  R.sup.11    X'Z         M                                   __________________________________________________________________________     H         H        CH.sub.3    NHC.sub.2 H.sub.4                                                                          K                                   H         "        C(CH.sub.3).sub.3                                                                          "           "                                   H         "        CF.sub.3    "           "                                   H         "        COOC.sub.2 H.sub.5                                                                         "           "                                   H         "        CONHC.sub.2 H.sub.4 OSO.sub.3 Na                                                           "           Na                                  H         "        C.sub.6 H.sub.5                                                                            "           K                                   CH.sub.3  C.sub.6 H.sub.5                                                                         CH.sub.3    "           "                                   SO.sub.2 CH.sub.3                                                                        "        C(CH.sub.3).sub.3                                                                          "           "                                   Cl        "        C.sub.6 H.sub.5                                                                            "           Na                                  C.sub.6 H.sub.5                                                                          "        "           "           "                                   Br        C.sub.6 H.sub. 5 SO.sub.2                                                               CH.sub.3    "           "                                   C.sub.2 H.sub.5                                                                          "        "           N(CH.sub.3)C.sub.2 H.sub.4                                                                 "                                   C.sub.6 H.sub.4o-OCH.sub. 3                                                              "        "           N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          "                                   C.sub.6 H.sub.4o-Cl                                                                      H        "           NHC.sub.2 H.sub.4                                                                          K                                   C.sub.6 H.sub.4o-CH.sub. 3                                                               "        C.sub.6 H.sub.4p-OCH.sub.3                                                                 "           "                                   C.sub.6 H.sub.4o-C.sub. 2 H.sub.5                                                        "        CF.sub.3    "           "                                   C.sub.6 H.sub.4o-Br                                                                      "        COOC.sub.2 H.sub.5                                                                         "           "                                   C.sub.6 H.sub.4o-OC.sub. 2 H.sub.5                                                       "                                                                                        ##STR53##  "           Na                                  C.sub.6 H.sub.4m-CH.sub.3                                                                "        C.sub.6 H.sub.5                                                                            "           K                                   C.sub.6 H.sub.4m-OCH.sub.3                                                               C.sub.6 H.sub.5                                                                         C.sub.6 H.sub.4p-Br                                                                        "           "                                   C.sub.6 H.sub.4m-C.sub.2 H.sub.5                                                         "        C(CH.sub.3).sub.3                                                                          "           "                                   C.sub.6 H.sub.4m-Cl                                                                      "        C.sub.6 H.sub.11                                                                           "           Na                                  H         "        C.sub.6 H.sub.5                                                                            "           "                                   H         C.sub.6 H.sub.5 SO.sub.2                                                                CH.sub.3    N(CH.sub.3)C.sub.2 H.sub.4                                                                 "                                   H         C.sub.2 H.sub.5 SO.sub.2                                                                "           NHC.sub.2 H.sub.4                                                                          K                                   H         CH.sub.3 CO                                                                             "           N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          "                                   H         C.sub.6 H.sub.5 CO                                                                      "           NHC.sub.2 H.sub.4                                                                          "                                   H         CH.sub.3 CONH.sub.2  NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              "                                   C.sub.6 H.sub.5p-CH.sub.3                                                                C.sub.2 H.sub.4 OH                                                                      C.sub.2 H.sub.5                                                                            OC.sub.2 H.sub.4                                                                           "                                   C.sub.6 H.sub.5p-OCH.sub.3                                                               C.sub.2 H.sub.4 CN                                                                      "           NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         "                                   C.sub.6 H.sub.5p-Cl                                                                      C.sub.2 H.sub.4 OCOCH.sub.3                                                             "           NHC.sub.2 H.sub.4                                                                          "                                   C.sub.6 H.sub.5p-Br                                                                      C.sub.6 H.sub.11                                                                        CF.sub.3    OC.sub.2 H.sub.4                                                                           "                                   H         C.sub.2 H.sub.4 OH                                                                      C.sub.6 H.sub.4p-Cl                                                                        "           "                                   H         CH.sub.2 C.sub.6 H.sub.5                                                                CONHC.sub.2 H.sub.5                                                                        NHC.sub.3 H.sub.6                                                                          "                                   H         C.sub.2 H.sub.4 CN                                                                      CH(CH.sub.3).sub.2                                                                         OC.sub.2 H.sub.4                                                                           "                                   H         C.sub.2 H.sub.5                                                                         "           NHC.sub.2 H.sub.4                                                                          "                                   H         C.sub.2 H.sub.4 NHCOCH.sub.3                                                            C.sub.2 H.sub.5                                                                            "           "                                   H         C.sub.2 H.sub.4 CONH.sub.2                                                              CH.sub.3    "           "                                   H         C.sub.2 H.sub.4 NHCOCH.sub.3                                                            C.sub.2 H.sub.5                                                                            "           "                                   CH.sub.3  "        C.sub.6 H.sub.5                                                                            "           "                                   __________________________________________________________________________

                                      TABLE 17                                     __________________________________________________________________________      ##STR54##                                                                     R        Q  Q' R.sup.12   R.sup.13                                                                              X'Z    M                                      __________________________________________________________________________     H        CO CO C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.5                                                                       NHC.sub.2 H.sub.4                                                                     Na                                     H        CO CO NH.sub.2   CH.sub.3                                                                               "     "                                      H        CN CO --         NHCO.sub.2 C.sub.2 H.sub.5                                                            OC.sub.2 H.sub.4                                                                      K                                      H        CN CO --         CH.sub.2 OH                                                                           NHC.sub.2 H.sub.4                                                                     Na                                     H        CN CO --         CH.sub.3                                                                              OC.sub.2 H.sub.4                                                                      Na                                     H        CO SO.sub.2                                                                          NH.sub.2   OC.sub.6 H.sub.5                                                                      NHC.sub.2 H.sub.4                                                                     Na                                     CH.sub.3 CO SO.sub.2                                                                          CH.sub.2 Cl                                                                               OCH.sub.3                                                                             NHC.sub.2 H.sub.4                                                                     Na                                     SO.sub.2 CH.sub.3                                                                       CN SO.sub.2                                                                          --         C.sub.6 H.sub.5                                                                       NHC.sub.2 H.sub.4                                                                     Na                                     Cl       CO CO CH.sub.2 C(CH.sub. 3).sub.2 CH.sub.2                                                             NHC.sub.2 H.sub.4                                                                     K                                      C.sub.6 H.sub.5                                                                         CO CO 1,2-C.sub.6 H.sub.4                                                                              NHC.sub.2 H.sub.4                                                                     K                                      Br       CO CO C.sub.2 H.sub.5                                                                           OC.sub.2 H.sub.5                                                                      NHC.sub.2 H.sub.4                                                                     K                                      C.sub.2 H.sub.5                                                                         CO CO CH.sub.3   NH.sub.2                                                                              N(CH.sub.3)C.sub.2 H.sub.4                                                            K                                      C.sub.6 H.sub.4o-OCH.sub.3                                                              CO CO NHC.sub.2 H.sub.5                                                                         NH.sub.2                                                                              N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                     K                                      C.sub.6 H.sub.4o-Cl                                                                     CO CO NHC.sub.2 H.sub.5                                                                         CH.sub.3                                                                              OC.sub.2 H.sub.4                                                                      K                                      C.sub.6 H.sub.4o-CH.sub.3                                                               CO SO.sub.2                                                                          NH.sub.2   C.sub.2 H.sub.5                                                                       OC.sub.2 H.sub.4                                                                      K                                      C.sub.6 H.sub.4o-C.sub.2 H.sub.5                                                        CO CO SC.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                       NHC.sub.2 H.sub.4                                                                     K                                      C.sub.6 H.sub.4o-Br                                                                     CO CO SCH.sub.2C.sub.6 H.sub.5                                                                  C.sub.2 H.sub.5                                                                       NHC.sub.2 H.sub.4                                                                     K                                      C.sub.6 H.sub.4o-OC.sub.2 H.sub.5                                                       CO CO SC.sub.6 H.sub.11                                                                         OCH.sub.3                                                                             NHC.sub.2 H.sub.4                                                                     K                                      C.sub.6 H.sub.4m-CH.sub.3                                                               CO CO C.sub.6 H.sub.5                                                                           OCH.sub.3                                                                             NHC.sub.2 H.sub.4                                                                     K                                      C.sub.6 H.sub.4m-OCH.sub.3                                                              CO CO NHCOC.sub.2 H.sub.5                                                                       NHCO.sub.2 C.sub.2 H.sub.5                                                            NHC.sub.2 H.sub.4                                                                     K                                      C.sub.6 H.sub.4m-C.sub.2 H.sub.5                                                        CO CO NHSO.sub.2 C.sub.2 H.sub.5                                                                NHCO.sub.2 C.sub.2 H.sub.5                                                            NHC.sub.2 H.sub.4                                                                     K                                      C.sub.6 H.sub.4m-Cl                                                                     CO CO NHCOC.sub.6 H.sub.5                                                                       NHCO.sub.2 C.sub.2 H.sub.5                                                            NHC.sub.2 H.sub.4                                                                     K                                      H        CO CO OC.sub.2 H.sub.5                                                                          NHCO.sub.2 C.sub.2 H.sub.5                                                            NHC.sub.2 H.sub.4                                                                     K                                      __________________________________________________________________________

                                      TABLE 18                                     __________________________________________________________________________      ##STR55##                                                                              OH                                                                    R        Position                                                                            R.sup.2   X'Z         M                                          __________________________________________________________________________     H        2    5-Cl      NHC.sub.2 H.sub.4                                                                          Na                                         H        2    5-Cl      NHC(CH.sub.3).sub.2 CH.sub.2                                                               Na                                         H        2    5-OCH.sub.3                                                                              NHC(CH.sub.3).sub.2 CH.sub.2                                                               Na                                         H        3,4  H         "           K                                          H        2    5-OCH.sub.3                                                                              "           Na                                         H        2    "         NHC.sub.2 H.sub.4                                                                          "                                          CH.sub.3 2    5-CH.sub.3                                                                               NHC.sub.2 H.sub.4                                                                          "                                          SO.sub.2 CH.sub.3                                                                       3,4  H         "           "                                          Cl       2    5-OCH.sub.3                                                                              "           K                                          C.sub.6 H.sub.5                                                                         2    "         "           NH.sub.4                                   Br       2    5-NHC.sub.6 H.sub.5                                                                      OC.sub.2 H.sub.4                                                                           Na                                         C.sub.2 H.sub.5                                                                         2    "         OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                          Na                                         C.sub.6 H.sub.4o-OCH.sub.3                                                              2    5-NHCOCH.sub.3                                                                           NHC.sub.2 H.sub.4                                                                          Na                                         C.sub.6 H.sub.4o-Cl                                                                     2    5-NHCOCH.sub.3                                                                           OC.sub.2 H.sub.4                                                                           Na                                         C.sub.6 H.sub.4o-CH.sub.3                                                               2    "         OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                          Na                                         C.sub.6 H.sub.4o-C.sub.2 H.sub.5                                                        2    "         N(CH.sub.3)C.sub.2 H.sub.4                                                                 "                                          C.sub.6 H.sub.4o-Br                                                                     2    "         N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          "                                          C.sub.6 H.sub.4o-OC.sub.2 H.sub.5                                                       2    5-CH.sub.3                                                                               NHC.sub.2 H.sub.4                                                                          Na                                         C.sub.6 H.sub.4m-CH.sub.3                                                               2    "         OC.sub.2 H.sub.4                                                                           Na                                         C.sub.6 H.sub.4m-OCH.sub.3                                                              2    5-OCH.sub.3                                                                              NHC.sub.2 H.sub.4                                                                          K                                          C.sub.6 H.sub.4m-C.sub.2 H.sub.5                                                        2    5-Cl      "           Na                                         C.sub.6 H.sub.4m-Cl                                                                     2    5-Cl      "           Na                                         H        4    2-OCH.sub.3                                                                              "           K                                          H        4    2-OCH.sub.3                                                                              "           K                                          H        3,4  H         "           Na                                         H        3,4  H         "           Na                                         H        2    3-NHCOCH.sub.3                                                                           "           Na                                         H        2    "         N(CH.sub.3)C.sub.2 H.sub.4                                                                 K                                          C.sub.6 H.sub.5p-CH.sub.3                                                               2                                                                                    ##STR56##                                                                               NHC.sub.2 H.sub.4                                                                          K                                                        C.sub.2 H.sub.4 OSO.sub.3 K                                      C.sub.6 H.sub.4p-OCH.sub.3                                                              2    5-C.sub.6 H.sub.11                                                                       NHC.sub.2 H.sub.4                                                                          "                                          C.sub.6 H.sub.4p-Cl                                                                     2    5-OC.sub.6 H.sub.5                                                                       N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          "                                          C.sub.6 H.sub.4p-Br                                                                     2    5-SCH.sub.3                                                                              NHC.sub.2 H.sub.4                                                                          K                                          H        2    5-SC.sub.6 H.sub.5                                                                       NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              K                                          H        2    5-NHCOOCH.sub.3                                                                          OC.sub.2 H.sub.4                                                                           Na                                         H        2    5-NHSO.sub.2 CH.sub.3                                                                    NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         Na                                         H        2    5-NHCOCH.sub.3                                                                           NHC.sub.2 H.sub.4                                                                          NH.sub.4                                   H        2    5-NHCOCH.sub.2 Cl                                                                        OC.sub.2 H.sub.4                                                                           K                                          H        2    5-NHCOC.sub.2 H.sub.4 OH                                                                 OC.sub.2 H.sub.4                                                                           K                                          H        2    5-Cl      NHC.sub.3 H.sub.6                                                                          K                                          H        2    5-NHCONHC.sub.2 H.sub.5                                                                  OC.sub.2 H.sub.4                                                                           NH.sub.4                                   H        2    5-NHCON(C.sub.2 H.sub.5).sub.2                                                           NHC.sub.2 H.sub.4                                                                          K                                          CH.sub.3 2    5-CH.sub.3                                                                               "           "                                          SO.sub.2 CH.sub.3                                                                       2    5-NHCOCH.sub.3                                                                           "           "                                          Cl       4    H         "           Na                                         __________________________________________________________________________

                                      TABLE 19                                     __________________________________________________________________________      ##STR57##                                                                              OH                                                                    R        Position                                                                            R.sup.2  R.sup.14   X'Z         M                                __________________________________________________________________________     H        2    3-CO.sub.2 CH.sub.3                                                                     H          OC.sub.2 H.sub.4                                                                           K                                H        4    H        H          "           "                                H        4    H        H          "           "                                H        4    H        H          NHC.sub.3 H.sub.6 OC.sub.2 H.sub.4                                                         Na                               H        2    H        H          NHC.sub.2 H.sub.4                                                                          K                                H        2    3-CONH.sub.2                                                                            H          "           K                                CH.sub.3 2    3-CO.sub.2 CH.sub.3                                                                     H          OC.sub.2 H.sub.4                                                                           Na                               SO.sub.2 CH.sub.3                                                                       2    H        6-SO.sub.2 N(CH.sub.3).sub.2                                                              NHC.sub.2 H.sub.4 NHC.sub.2 H.sub.                                                         Na                               Cl       2    "        6-SO.sub.2 NHC.sub.3 H.sub.6 OCH.sub.3                                                    OC.sub.2 H.sub.4                                                                           Na                               C.sub.6 H.sub.4                                                                         2    "        6-SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                       OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                          "                                Br       2    "        H          NHC.sub.2 H.sub.4                                                                          "                                C.sub.2 H.sub.4                                                                         4    "        "          N(CH.sub.3)C.sub.2 H.sub.4                                                                 "                                C.sub.6 H.sub.4o-OCH.sub.3                                                              2    "        "          N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          "                                C.sub.6 H.sub.4o-Cl                                                                     2    3-CONH.sub.2                                                                            "          NHC.sub.2 H.sub.4                                                                          K                                C.sub.6 H.sub.4o-CH.sub.3                                                               2    "        "          NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              K                                C.sub.6 H.sub.4o-C.sub.2 H.sub.5                                                        2    3-CO.sub.2 CH.sub.3                                                                     "          OC.sub.2 H.sub.4                                                                           Na                               C.sub.6 H.sub.4o-Br                                                                     2    "        "          NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         Na                               C.sub.6 H.sub.4o-OC.sub.2 H.sub.5                                                       2    H        "          NHC.sub.2 H.sub.4                                                                          NH.sub.4                         C.sub.6 H.sub.4m-CH.sub.3                                                               2    3-CO.sub.2 CH.sub.2 Cl                                                                  "          OC.sub.2 H.sub.4                                                                           K                                C.sub.6 H.sub.4m-OCH.sub.3                                                              2    3-CO.sub.2 C.sub.2 H.sub.4 OH                                                           "          OC.sub.2 H.sub.4                                                                           K                                C.sub.6 H.sub.4m-C.sub.2 H.sub.5                                                        4    H        H          NHC.sub.3 H.sub.6                                                                          K                                C.sub.6 H.sub.4m-Cl                                                                     2    3-CONHC.sub.2 H.sub.5                                                                   "          OC.sub.2 H.sub.4                                                                           NH.sub.4                         H        2    3-CON(C.sub.2 H.sub.5).sub.2                                                            "          NHC.sub.2 H.sub.4                                                                          K                                H        2    3-CO.sub.2 C.sub.2 H.sub.5                                                              "          "           "                                H        2    3-CO.sub.2 CH(CH.sub.3).sub.2                                                           "          "           "                                H        2    H        "          N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          "                                __________________________________________________________________________

                                      TABLE 20                                     __________________________________________________________________________      ##STR58##                                                                     R        R.sup.16      R.sup.17 R.sup.2                                                                             R.sup.14                                                                            X'Z         M                        __________________________________________________________________________     H        C.sub.6 H.sub.11                                                                             H        H    H    OC.sub.2 H.sub.4                                                                           K                        H        C.sub.2 H.sub.4 CONH.sub.2                                                                   H        H    H    "           "                        H        C.sub.2 H.sub.4 SO.sub.2 CHCH.sub.2                                                          H        H    8-OH "           "                        H        C.sub.2 H.sub.4 NHSO.sub.2 CH.sub.3                                                          H        H    H    NHC.sub.3 H.sub.6 OC.sub.2                                                     H.sub.4     Na                                 ##STR59##    H        3-OCH.sub.3                                                                         8-OH NHC.sub.2 H.sub.4                                                                          K                        H        C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3                                                   H        H    H    "           K                        CH.sub.3 CH(CH.sub.3)C.sub.2 H.sub.5                                                                  H        H    H    OC.sub.2 H.sub.4                                                                           Na                       SO.sub.2 CH.sub.3                                                                       CH(CH.sub.3)CH.sub.2 CH(CH.sub.3)CH.sub.3                                                    H        H    H    NHC.sub.2 H.sub.4 NHC.sub.2                                                    H.sub.4     Na                       Cl       C.sub.6 H.sub.5                                                                              C.sub.2 H.sub.4 OH                                                                      2-OCH.sub.3                                                                         H    OC.sub.2 H.sub.4                                                                           Na                       C.sub.6 H.sub.5                                                                         C.sub.2 H.sub.5                                                                              H        "    H    OC.sub.2 H.sub.4 OC.sub.2                                                      H.sub.4     "                        Br       CH.sub.2 CH(OH)CH.sub.2 OH                                                                   H        "    H    NHC.sub.2 H.sub.4                                                                          "                        C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4 SO.sub.2 NH.sub.2                                                            H        "    "    N(CH.sub.3)C.sub.2 H.sub.4                                                                 "                        C.sub.6 H.sub.4o-OCH.sub.3                                                              (CH.sub.2).sub.6 NHCOCH.sub.3                                                                H        "    "    N(C.sub.6 H.sub.5)C.sub.2                                                      H.sub.4     "                        C.sub.6 H.sub.4o-Cl                                                                     C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                          H        H    H    NHC.sub.2 H.sub.4                                                                          K                        C.sub.6 H.sub.4o-CH.sub.3                                                               CH.sub.2 C.sub.6 H.sub.5                                                                     CH.sub.2 C.sub.6 H.sub.5                                                                "    "    NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              K                        C.sub.6 H.sub.4o-C.sub.2 H.sub.5                                                        CH.sub.3      H        H    "    OC.sub.2 H.sub.4                                                                           Na                       C.sub.6 H.sub.4o-Br                                                                     C.sub.6 H.sub.11                                                                             H        "    "    NHC.sub.2 H.sub.4 OC.sub.2                                                     H.sub.4     Na                       C.sub.6 H.sub.5OOC.sub.2 H.sub.5                                                        C.sub.2 H.sub.4 CONH.sub.2                                                                   H        H    "    NHC.sub.2 H.sub.4                                                                          NH.sub.4                 C.sub.6 H.sub.4m-CH.sub.3                                                               C.sub.2 H.sub.4 SO.sub.2 CHCH.sub.2                                                          H        H    8-OCH.sub.3                                                                         OC.sub.2 H.sub.4                                                                           K                        C.sub.6 H.sub.4m-OCH.sub.3                                                               ##STR60##    H        3-OC.sub.2 H.sub.5                                                                  8-OC.sub.2 H.sub.5                                                                  OC.sub.2 H.sub.4                                                                           K                        C.sub.6 H.sub.4m-C.sub.2 H.sub.5                                                         ##STR61##    H        H    H    NHC.sub.3 H.sub.6                                                                          K                        C.sub.6 H.sub.4m-Cl                                                                     C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3                                                   CH.sub. 3                                                                               H    "    OC.sub.2 H.sub.4                                                                           NH.sub.4                 H        CH(CH.sub.3)C.sub.2 H.sub.5                                                                  CH.sub.3 H    "    NHC.sub.2 H.sub.4                                                                          K                        H        CH(CH.sub.3)CH.sub.2 CH(CH.sub.3)CH.sub.3                                                    CH.sub.3 3-C.sub.2 H.sub.5                                                                   "    "           "                        H        C.sub.6 H.sub.5                                                                              CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                      H    "    "           "                        H        C.sub.2 H.sub.5                                                                              "        H    "    N(C.sub.6 H.sub.5)C.sub.2                                                      H.sub.4     "                        __________________________________________________________________________

The invention has been described in detail with particular reference to certain preferred embodiments thereof, but it will be understood that variations and modifications can be effected within the spirit and scope of the invention. 

We claim:
 1. A dye of the formula: ##STR62## wherein R¹ is selected from hydrogen, alkyl, cyclohexyl, 2-thienyl, 2-furyl, phenyl, and phenyl substituted with alkoxy, thiocyano, alkylthio, carbamoyl, alkylcarbamoyl, alkanoyl, alkylsulfonyl, sulfamoyl, SO₂ NH(alkyl), SO₂ N(dialkyl), alkylsulfonamido, alkanoylamino, halogen, trifluoromethyl or SO₃ (aryl); R is selected from hydrogen, halogen, alkyl, alkylsulfonyl, phenyl, and phenyl substituted with alkyl, alkoxy or halogen; C is a coupler selected from ##STR63## wherein R² and R¹⁴ each represents up to three groups selected from hydrogen, fluorine, chlorine, bromine, alkyl, cycloalkyl, alkoxy, phenoxy, alkylthio, arylthio, and radicals having the formula --NH--X--R³ in which X is --CO--, --COO--, or --SO₂ -- and R³ is selected from alkyl and alkyl substituted with halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyloxy, and alkoxy, and when X is --CO--, R³ also is selected from hydrogen, amino, alkylamino, dialkylamino, arylamino, aryl, and furyl;R⁴ and R⁵ are each selected from hydrogen, alkyl, aryl, cycloalkyl, and alkyl substituted with halogen, CN, OH, alkoxy, aryloxy, alkoxyalkoxy, alkanoyl, alkanoyloxy, carbamoyl, alkylcarbamoyl, sulfamoyl, alkylsulfamoyl, alkoxyalkanoyloxy, and cycloalkyl, and R⁴ and R⁵ together represent a single, combined group --CH₂ CH₂ CH₂ CH₂ CH₂ --, --CH₂ CH₂ OCH₂ CH₂ --, --CH₂ CH₂ --S--CH₂ CH₂ --, or --CH₂ CH₂ --SO₂ --CH₂ CH₂ --, R⁸ represents one or two groups each selected from hydrogen, alkyl and alkyl substituted with --CN, alkoxy, alkoxycarbonyl, alkoxycarbonyloxy, phenyl, cyclohexoxy, --OH, --Cl and Br; R⁹, R¹⁰ and R¹¹ are each selected from hydrogen, alkyl, phenyl, or phenyl substituted with 1-3 groups selected from Cl, Br, alkyl or alkoxy, alkylthio, benzylthio, cyclohexylthio and phenylthio; Q and Q' are each selected from --CO--, --SO₂ --, or --CN; R¹² and R¹³ are each selected from alkyl, hydroxyalkyl, alkoxy, alkoxycarbonylamino, trifluoromethyl, phenyl or phenyl substituted with 1-3 groups selected from Cl, Br, alkyl or alkoxy, alkoxycarbonylalkyl, cyanoalkyl, amino, haloalkyl, alkylamino, alkylthio, benzylthio, cyclohexylthio and phenylthio; and R¹² and R¹³ together comprise --CH₂ C(CH₃)₂ CH₂ --, or 1,2--C₆ H₄ -- connecting Q and Q'; R¹⁶ and R¹⁷ are selected from hydrogen, cycloalkyl, aryl, alkyl, and alkyl substituted with alkoxy, hydroxy, alkoxyalkoxy, hydroxyalkoxy, carbamoyl, sulfamoyl, alkanoylamino, or alkenylsulfonyl, and aryl substituted with hydroxyalkyl; e is 1 or 2; t and t' are each 1 or zero; X' is O, NH, N(alkyl)-, or N(aryl)-; Z is selected from straight- or branched-chain alkylene, and such alkylene substituted with phenyl, halogen, OSO₃ M, alkoxy or aryloxy groups, --CH₂ (CH₂)_(m) V--CH₂ (CH₂)_(p) --, where m is 1, 2 or 3, p is 0, 1, 2 or 3, and V is O, S, SO₂, --SO₂ NH--, --SO₂ N(alkyl)-, --SO₂ N(aryl), --N(SO₂ aryl)-, --NH, --NHCO--, --NHCONH, --N(SO₂ alkyl), or --CON(alkyl); M is H, Na, K or NH₄ ; n is 1 or 2; and wherein each of the above alkyl and alkoxy groups contain from 0 to three of the following: hydroxy; halogen; cyano; succinimido; glutarimido; phthalimido; 2-pyrrolidono; cyclohexyl; phenyl or phenyl substituted with alkyl, alkoxy, halogen, alkanoylamino, cyano or alkoxycarbonyl; alkanoylamino; sulfamoyl; alkylsulfamoyl; vinylsulfonyl; acrylamido; phthalimidinyl; benzosulfonicimidyl; alkylsulfonamido; phenylsulfonamido; alkoxycarbonylamino; alkylcarbamoylxoy; alkoxycarbonyl; alkoxycarbonyloxy; ##STR64## wherein Y is --NH--, --NH--alkyl-, --O--, --S--, or --CH₂ O--; --S--R⁶, wherein R⁶ is alkyl, phenyl, phenyl substituted with halogen, alkyl, alkoxy, alkanoylamino, cyano, or alkoxycarbonyl, pyridyl, pyrimidinyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, or ##STR65## --SO₂ R³ ; --COOR³ ; --OXR³, --NH--X--R³ ; --X--R³ ; --SO₂ NR⁷ R⁷ ; wherein R³ and X are as defined above and each R⁷ is selected from H and R³ ; alkoxy; alkoxy substituted with hydroxy, cyano, alkanoyloxy, or alkoxy; phenoxy; or phenoxy substituted with one or more of alkyl, alkoxy or halogen.
 2. The dye according to claim 1 of the formula ##STR66##
 3. The dye according to claim 1 of the formula ##STR67## 